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1030825-20-7

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  • High Quality 99% 1030825-20-7 2-((5-bromo-2-methylphenyl)methyl)-5-(4-fluorophenyl)thiophene Manufacturer

    Cas No: 1030825-20-7

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  • 2-(5-BroMo-2-Methylbenzyl)-5-(4-fluorophenyl)thiophene CAS 1030825-20-7 IN STOCK Canagliflozin Intermediate 1030825-20-7

    Cas No: 1030825-20-7

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1030825-20-7 Usage

Uses

2-[(5-Bromo-2-methylphenyl)methyl]-5-(4-fluorophenyl)thiophene is an antidiabetic agent that can be used to prepare Canagliflozin (C175190), a sodium-dependent glucose co-transporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes mellitus.

Check Digit Verification of cas no

The CAS Registry Mumber 1030825-20-7 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,0,3,0,8,2 and 5 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 1030825-20:
(9*1)+(8*0)+(7*3)+(6*0)+(5*8)+(4*2)+(3*5)+(2*2)+(1*0)=97
97 % 10 = 7
So 1030825-20-7 is a valid CAS Registry Number.
InChI:InChI=1S/C18H14BrFS/c1-12-2-5-15(19)10-14(12)11-17-8-9-18(21-17)13-3-6-16(20)7-4-13/h2-10H,11H2,1H3

1030825-20-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-[(5-bromo-2-methylphenyl)methyl]-5-(4-fluorophenyl)thiophene

1.2 Other means of identification

Product number -
Other names 2-(5-Bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiophene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1030825-20-7 SDS

1030825-20-7Synthetic route

(5-bromo-2-methylphenyl)[5-(p-fluorophenyl)thiophene-2-yl]methanone
1132832-75-7

(5-bromo-2-methylphenyl)[5-(p-fluorophenyl)thiophene-2-yl]methanone

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran at -20 - -10℃; for 48h; Reagent/catalyst; Temperature; Concentration; Solvent;97.7%
With hydrogen In isopropyl alcohol at 100℃; under 22502.3 Torr; for 5h; Reagent/catalyst; Temperature; Pressure; Autoclave;97%
Stage #1: (5-bromo-2-methylphenyl)[5-(p-fluorophenyl)thiophene-2-yl]methanone With aluminum (III) chloride In tetrahydrofuran at 0 - 5℃; for 0.5h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran Reflux;
92%
para-bromotoluene
106-38-7

para-bromotoluene

2-chloromethyl-5-(4-fluorophenyl)thiophene

2-chloromethyl-5-(4-fluorophenyl)thiophene

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With aluminum (III) chloride In ethyl acetate at 80℃; for 8h; Cooling with ice;87%
5-(5-bromo-2-methylphenyl)-1-(4-fluorophenyl)pentane-1,4-dione

5-(5-bromo-2-methylphenyl)-1-(4-fluorophenyl)pentane-1,4-dione

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With Lawessons reagent In toluene for 4h; Solvent; Reflux;86%
With phosphorus trisulfide In diphenylether at 170 - 180℃; for 2h;63%
2-(4-fluorophenyl)-5-((5-amino-2-methylphenyl)methyl)thiophene

2-(4-fluorophenyl)-5-((5-amino-2-methylphenyl)methyl)thiophene

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Stage #1: 2-(4-fluorophenyl)-5-((5-amino-2-methylphenyl)methyl)thiophene With nitrous acid isobutyl ester; copper(I) bromide In acetone for 1h; Sandmeyer Reaction; Cooling with ice;
Stage #2: With hydrogen bromide In water at 90℃; for 1h; Temperature;
84%
Stage #1: 2-(4-fluorophenyl)-5-((5-amino-2-methylphenyl)methyl)thiophene With nitrous acid isobutyl ester; copper(I) bromide In acetone at -5℃; for 1h; Sandmeyer Reaction;
Stage #2: With hydrogen bromide In water at 80℃; for 2h; Temperature;
82%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

1-bromo-3-(chloromethyl)-4-methylbenzene
87604-18-0

1-bromo-3-(chloromethyl)-4-methylbenzene

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With zinc(II) chloride In ethyl acetate for 6h; Reflux; Large scale;78%
para-bromotoluene
106-38-7

para-bromotoluene

2-bromomethyl-5-(4-fluorophenyl)thiophene

2-bromomethyl-5-(4-fluorophenyl)thiophene

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With zinc(II) chloride at 70℃; for 3h;73%
1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate / tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / ethanol; water / 90 °C / Inert atmosphere
2.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C
2.2: cooling with ice
3.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane; acetonitrile / 3 h / 0 - 20 °C
View Scheme
Multi-step reaction with 5 steps
1: potassium acetate; palladium diacetate / N,N-dimethyl acetamide / 22 h / 140 - 150 °C
2: sodium dihydrogenphosphate; dihydrogen peroxide; sodium chlorite / acetonitrile; water / 1.5 h / 40 °C
3: thionyl chloride / toluene / 21 h / 90 °C
4: iron(III) chloride / dichloromethane / 20 h / 20 °C
5: triethylsilane; boron trifluoride diethyl etherate / acetonitrile; dichloromethane / 26 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium propionate; bis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium (II) Dichloride / Isopropyl acetate / Reflux
2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / Dimethyl ether; water / 70 - 75 °C
3.1: thionyl chloride / N,N-dimethyl-formamide; dichloromethane / 0 - 35 °C
3.2: 0 - 35 °C
4.1: aluminum (III) chloride / tetrahydrofuran / 0.5 h / 0 - 5 °C
4.2: Reflux
View Scheme
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C
1.2: cooling with ice
2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane; acetonitrile / 3 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.1 h / 25 - 30 °C / Inert atmosphere
1.2: 0 - 15 °C / Inert atmosphere
2.1: aluminum (III) chloride; sodium tetrahydroborate / 1,2-dimethoxyethane / 0 - 70 °C
View Scheme
Multi-step reaction with 2 steps
1.1: oxalyl dichloride / dichloromethane / 2 h / 20 °C
1.2: 4 h / -15 - 35 °C
2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane; acetonitrile / 0 - 35 °C
View Scheme
5-bromo-2-methylbenzoyl chloride
21900-41-4

5-bromo-2-methylbenzoyl chloride

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C
1.2: cooling with ice
2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane; acetonitrile / 3 h / 0 - 20 °C
View Scheme
5-bromo-2-methylbenzoic acid
79669-49-1

5-bromo-2-methylbenzoic acid

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 6 h / 20 °C
2.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C
2.2: cooling with ice
3.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane; acetonitrile / 3 h / 0 - 20 °C
View Scheme
5-(4-fluorophenyl)thiophene-2-carboxylic acid
115933-30-7

5-(4-fluorophenyl)thiophene-2-carboxylic acid

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / toluene / 21 h / 90 °C
2: iron(III) chloride / dichloromethane / 20 h / 20 °C
3: triethylsilane; boron trifluoride diethyl etherate / acetonitrile; dichloromethane / 26 h / 0 - 20 °C
View Scheme
5-(4-fluorophenyl)thiophene-2-carbonyl chloride
918487-45-3

5-(4-fluorophenyl)thiophene-2-carbonyl chloride

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iron(III) chloride / dichloromethane / 20 h / 20 °C
2: triethylsilane; boron trifluoride diethyl etherate / acetonitrile; dichloromethane / 26 h / 0 - 20 °C
View Scheme
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium acetate; palladium diacetate / N,N-dimethyl acetamide / 22 h / 140 - 150 °C
2: sodium dihydrogenphosphate; dihydrogen peroxide; sodium chlorite / acetonitrile; water / 1.5 h / 40 °C
3: thionyl chloride / toluene / 21 h / 90 °C
4: iron(III) chloride / dichloromethane / 20 h / 20 °C
5: triethylsilane; boron trifluoride diethyl etherate / acetonitrile; dichloromethane / 26 h / 0 - 20 °C
View Scheme
5-(4-fluorophenyl)thiophene-2-carboxaldehyde
249504-38-9

5-(4-fluorophenyl)thiophene-2-carboxaldehyde

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium dihydrogenphosphate; dihydrogen peroxide; sodium chlorite / acetonitrile; water / 1.5 h / 40 °C
2: thionyl chloride / toluene / 21 h / 90 °C
3: iron(III) chloride / dichloromethane / 20 h / 20 °C
4: triethylsilane; boron trifluoride diethyl etherate / acetonitrile; dichloromethane / 26 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium tetrahydroborate; ethanol / 6 h / 20 °C
2: thionyl chloride / 3 h / 70 °C
3: aluminum (III) chloride / ethyl acetate / 8 h / 80 °C / Cooling with ice
View Scheme
4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / 25 - 75 °C / Inert atmosphere
2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.1 h / 25 - 30 °C / Inert atmosphere
2.2: 0 - 15 °C / Inert atmosphere
3.1: aluminum (III) chloride; sodium tetrahydroborate / 1,2-dimethoxyethane / 0 - 70 °C
View Scheme
Multi-step reaction with 4 steps
1: tetrabutylammomium bromide; palladium diacetate; potassium carbonate / water / 2 h / 20 °C
2: sodium tetrahydroborate; ethanol / 6 h / 20 °C
3: thionyl chloride / 3 h / 70 °C
4: aluminum (III) chloride / ethyl acetate / 8 h / 80 °C / Cooling with ice
View Scheme
Multi-step reaction with 3 steps
1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium carbonate; tricyclohexylphosphine / N,N-dimethyl-formamide / 10 h / 90 °C
2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chloroform / 3 h / Reflux
3: zinc(II) chloride / 3 h / 70 °C
View Scheme
2-methyl-5-nitrobenzoyl chloride
64688-68-2

2-methyl-5-nitrobenzoyl chloride

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tricyclohexylphosphine; potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0) / ethanol; water / 24 h / 90 °C
2.1: tricyclohexylphosphine; potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0) / ethanol; water / 24 h / 90 °C
3.1: magnesium / ethanol / 2 h / 80 °C
4.1: copper(I) bromide; nitrous acid isobutyl ester / acetone / 1 h / Cooling with ice
4.2: 1 h / 90 °C
View Scheme
(5-bromothiophen-2-yl)(2-methyl-5-nitrophenyl)methanone

(5-bromothiophen-2-yl)(2-methyl-5-nitrophenyl)methanone

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tricyclohexylphosphine; potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0) / ethanol; water / 24 h / 90 °C
2.1: magnesium / ethanol / 2 h / 80 °C
3.1: copper(I) bromide; nitrous acid isobutyl ester / acetone / 1 h / Cooling with ice
3.2: 1 h / 90 °C
View Scheme
5-bromo-2-methylbenzaldehyde
90050-59-2

5-bromo-2-methylbenzaldehyde

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate / Reflux
2: 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; N-ethyl-N,N-diisopropylamine / toluene / 8 h / Reflux
3: Lawessons reagent / toluene / 4 h / Reflux
View Scheme
fluorobenzene
462-06-6

fluorobenzene

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: aluminum (III) chloride / dichloromethane / 2 h / Cooling with ice; Reflux
2.1: tetraphosphorus decasulfide / toluene / 0.5 h / Microwave irradiation
3.1: oxalyl dichloride / dichloromethane / 2 h / 20 °C
3.2: 4 h / -15 - 35 °C
4.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane; acetonitrile / 0 - 35 °C
View Scheme
4-(4-fluorophenyl)-4-oxopropionic acid
366-77-8

4-(4-fluorophenyl)-4-oxopropionic acid

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetraphosphorus decasulfide / toluene / 0.5 h / Microwave irradiation
2.1: oxalyl dichloride / dichloromethane / 2 h / 20 °C
2.2: 4 h / -15 - 35 °C
3.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane; acetonitrile / 0 - 35 °C
View Scheme
5-bromo-2-thiophencarboxaldehyde
4701-17-1

5-bromo-2-thiophencarboxaldehyde

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrabutylammomium bromide; palladium diacetate; potassium carbonate / water / 2 h / 20 °C
2: sodium tetrahydroborate; ethanol / 6 h / 20 °C
3: thionyl chloride / 3 h / 70 °C
4: aluminum (III) chloride / ethyl acetate / 8 h / 80 °C / Cooling with ice
View Scheme
[5-(4-fluorophenyl)thiophen-2-yl]methanol
1225916-69-7

[5-(4-fluorophenyl)thiophen-2-yl]methanol

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / 3 h / 70 °C
2: aluminum (III) chloride / ethyl acetate / 8 h / 80 °C / Cooling with ice
View Scheme
C14H17BrO3

C14H17BrO3

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: water; sodium hydroxide / methanol / 2 h / 35 - 40 °C
2.1: thionyl chloride / dichloromethane / 4 h / Reflux
2.2: 7.5 h / 0 °C
3.1: phosphorus trisulfide / diphenylether / 2 h / 170 - 180 °C
View Scheme
ethyl 5-bromo-4-oxopentanoate
14594-25-3

ethyl 5-bromo-4-oxopentanoate

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: aluminum (III) chloride / dichloromethane / 6 h / -2 - 2 °C
2.1: water; sodium hydroxide / methanol / 2 h / 35 - 40 °C
3.1: thionyl chloride / dichloromethane / 4 h / Reflux
3.2: 7.5 h / 0 °C
4.1: phosphorus trisulfide / diphenylether / 2 h / 170 - 180 °C
View Scheme
para-bromotoluene
106-38-7

para-bromotoluene

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: aluminum (III) chloride / dichloromethane / 6 h / -2 - 2 °C
2.1: water; sodium hydroxide / methanol / 2 h / 35 - 40 °C
3.1: thionyl chloride / dichloromethane / 4 h / Reflux
3.2: 7.5 h / 0 °C
4.1: phosphorus trisulfide / diphenylether / 2 h / 170 - 180 °C
View Scheme
2-bromo-5-methyl thiophene
765-58-2

2-bromo-5-methyl thiophene

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium carbonate; tricyclohexylphosphine / N,N-dimethyl-formamide / 10 h / 90 °C
2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chloroform / 3 h / Reflux
3: zinc(II) chloride / 3 h / 70 °C
View Scheme
2-Methylthiophene
554-14-3

2-Methylthiophene

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-Bromosuccinimide / tetrachloromethane / 6 h / Reflux
2.1: zinc(II) chloride / 7 h / 70 °C
3.1: palladium diacetate; potassium carbonate / N,N-dimethyl-formamide / 10 h / 90 °C
4.1: magnesium / ethanol / 2 h / 70 °C / Sealed tube
5.1: copper(I) bromide; nitrous acid isobutyl ester / acetone / 1 h / -5 °C
5.2: 2 h / 80 °C
View Scheme
2-bromo-5-(bromomethyl)-thiophene
59311-27-2

2-bromo-5-(bromomethyl)-thiophene

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: zinc(II) chloride / 7 h / 70 °C
2.1: palladium diacetate; potassium carbonate / N,N-dimethyl-formamide / 10 h / 90 °C
3.1: magnesium / ethanol / 2 h / 70 °C / Sealed tube
4.1: copper(I) bromide; nitrous acid isobutyl ester / acetone / 1 h / -5 °C
4.2: 2 h / 80 °C
View Scheme
2-bromo-5-[(5-nitro-2-methylphenyl)methyl]thiophene

2-bromo-5-[(5-nitro-2-methylphenyl)methyl]thiophene

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: palladium diacetate; potassium carbonate / N,N-dimethyl-formamide / 10 h / 90 °C
2.1: magnesium / ethanol / 2 h / 70 °C / Sealed tube
3.1: copper(I) bromide; nitrous acid isobutyl ester / acetone / 1 h / -5 °C
3.2: 2 h / 80 °C
View Scheme
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

5-bromo-2-methylbenzoic acid
79669-49-1

5-bromo-2-methylbenzoic acid

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: thionyl chloride / N,N-dimethyl-formamide; dichloromethane / 0 - 35 °C
1.2: 0 - 35 °C
2.1: aluminum (III) chloride / tetrahydrofuran / 0.5 h / 0 - 5 °C
2.2: Reflux
View Scheme
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-2-ol

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-2-ol

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at 20℃; for 3h;
99%
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

(3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1030825-21-8

(3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With sec-butylmagnesium chloride lithium chloride In tetrahydrofuran at -25 - -20℃; for 1h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at -25 - -20℃; for 2h; Inert atmosphere;
Stage #3: With methanesulfonic acid In tetrahydrofuran; methanol at -5 - 5℃; for 18h; Reagent/catalyst; Temperature; Inert atmosphere;
93.7%
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In tetrahydrofuran; hexane; toluene at -70 - -67℃; for 0.333333h;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -70 - -67℃; for 1h;
Stage #3: With methanol; methanesulfonic acid In tetrahydrofuran; hexane; toluene at 20℃; for 17h;
methanol
67-56-1

methanol

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

(3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1030825-21-8

(3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With iodine; magnesium In tetrahydrofuran at 0 - 25℃; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #3: methanol With methanesulfonic acid In tetrahydrofuran at 20℃; Temperature; Reagent/catalyst; Solvent; Inert atmosphere;
92.1%
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In tetrahydrofuran; hexane; toluene at -75 - -65℃; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -75 - -70℃;
Stage #3: methanol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at -75 - 30℃; for 12h;
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

2-(4-fluoro-phenyl)-5-(2-methyl-benzyl)-thiophene

2-(4-fluoro-phenyl)-5-(2-methyl-benzyl)-thiophene

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 0.5h;
Stage #2: With ammonium chloride In tetrahydrofuran; hexane; toluene at -78 - 20℃; for 0.5h;
88%
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 0.5h;
Stage #2: With ammonium chloride In tetrahydrofuran; hexane; toluene at -78 - 20℃; for 0.5h;
88%
methanol
67-56-1

methanol

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1358581-37-9

(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -78℃; for 3h;
Stage #3: methanol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at -78 - 40℃; for 10h;
83%
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

(2R,3S,4S,5S)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)hexane-1,2,3,4,5,6-hexaol

(2R,3S,4S,5S)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)hexane-1,2,3,4,5,6-hexaol

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In tetrahydrofuran at -80℃; for 0.5h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran for 1h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; Further stages;
81%
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

C70H82O6Si4

C70H82O6Si4

(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1358581-37-9

(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
With sec.-butyllithium In tetrahydrofuran; hexane; toluene at -78 - -65℃; for 2h; Inert atmosphere;77.8%
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

2,3,4,6-tetra-O-trimethylsilyl-D-glucono-1,5-lactone

2,3,4,6-tetra-O-trimethylsilyl-D-glucono-1,5-lactone

(2R,3S,4R,5R)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-2,3,4,5,6-pentahydroxyhexan-1-one

(2R,3S,4R,5R)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-2,3,4,5,6-pentahydroxyhexan-1-one

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In tetrahydrofuran; hexane; toluene at -80 - -70℃; for 1h; Inert atmosphere; Large scale;
Stage #2: 2,3,4,6-tetra-O-trimethylsilyl-D-glucono-1,5-lactone In tetrahydrofuran; toluene at -80 - -70℃; for 1h; Large scale;
Stage #3: With hydrogenchloride In tetrahydrofuran; water; toluene at 20℃; Solvent; Reagent/catalyst; Temperature; Large scale;
77.3%
methanesulfonic acid
75-75-2

methanesulfonic acid

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1358581-37-9

(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; hexane; toluene at -100 - -90℃; for 1h; Inert atmosphere;
Stage #2: methanesulfonic acid In tetrahydrofuran; methanol; hexane; toluene at -100 - 20℃;
77%
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

C18H42O6Si4

C18H42O6Si4

(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1358581-37-9

(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
With tert.-butyl lithium In tetrahydrofuran; toluene; pentane at -78 - -65℃; for 2h; Inert atmosphere;76.7%
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

3,4,6-tri-O-benzyl-D-glucal epoxide
74372-90-0

3,4,6-tri-O-benzyl-D-glucal epoxide

(2S,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3-ol

(2S,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3-ol

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With tri-n-butyllithium magnesate complex In tetrahydrofuran; diethyl ether; hexane at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: 3,4,6-tri-O-benzyl-D-glucal epoxide With copper(I) cyanide di(lithium chloride) In tetrahydrofuran; diethyl ether; hexane at 0 - 20℃; Inert atmosphere;
63%
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

1,6-anhydro-2,4-di-O-tert-butyldiphenylsilyl-β-D-glucopyranose
1432591-75-7

1,6-anhydro-2,4-di-O-tert-butyldiphenylsilyl-β-D-glucopyranose

2,4-di-O-tert-butyldiphenylsilyl-1-C-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-β-D-glucopyranoside
1432591-84-8

2,4-di-O-tert-butyldiphenylsilyl-1-C-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-β-D-glucopyranoside

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With magnesium In tetrahydrofuran; ethylene dibromide for 2h; Reflux;
Stage #2: With aluminum (III) chloride In tetrahydrofuran at 20℃; for 1h;
Stage #3: 1,6-anhydro-2,4-di-O-tert-butyldiphenylsilyl-β-D-glucopyranose With n-butyllithium In tetrahydrofuran; dibutyl ether at 20 - 150℃; for 5h;
56%
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

2-(azido(5-bromo-2-methylphenyl)methyl)-5-(4-fluorophenyl)thiophene

2-(azido(5-bromo-2-methylphenyl)methyl)-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With trimethylsilylazide; copper diacetate; (S,S)-4,4'-bis(phenylmethyl)-2,2',5,5'-tetrahydro-2,2'-bioxazole; N-fluorobis(benzenesulfon)imide In nitromethane at 30℃; for 48h; Inert atmosphere; Sealed tube;36%
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

3,5-bis-trifluromethylphenylboronic acid
73852-19-4

3,5-bis-trifluromethylphenylboronic acid

C26H16BrF7S

C26H16BrF7S

Conditions
ConditionsYield
With 3,4,7,8-Tetramethyl-o-phenanthrolin; copper (I) acetate; lithium carbonate; N-fluorobis(benzenesulfon)imide In N,N-dimethyl acetamide; benzene at 20℃; Inert atmosphere; Sealed tube;32%
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
898566-17-1

(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

Conditions
ConditionsYield
With sodium iodide; N,N`-dimethylethylenediamine; copper(l) iodide In diethylene glycol dimethyl ether; toluene at 110℃;
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In diethylene glycol dimethyl ether; toluene at 20℃; Inert atmosphere; Reflux;
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In diethylene glycol dimethyl ether; toluene for 36h; Inert atmosphere; Reflux;94.9 g
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

C36H57FO6SSi4

C36H57FO6SSi4

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In tetrahydrofuran; hexane; toluene at -70 - -67℃; for 0.5h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -70 - -67℃; for 1.5h; Inert atmosphere;
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

(4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one
110391-10-1

(4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one

(1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)cyclohex-2-enol
1413373-77-9

(1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)cyclohex-2-enol

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In tetrahydrofuran; hexane; toluene at -70℃; for 0.0833333h; Inert atmosphere;
Stage #2: (4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one In tetrahydrofuran; hexane; toluene at -70℃; for 0.25h;
Stage #3: With water In tetrahydrofuran; hexane; toluene
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

canagliflozin
842133-18-0

canagliflozin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / toluene; di-isopropyl ether; hexane / 0 °C / Inert atmosphere; Schlenk technique
1.2: 90 °C / Inert atmosphere; Schlenk technique
2.1: diisobutylaluminium hydride / toluene / 0.12 h / 20 °C / Inert atmosphere; Schlenk technique
2.2: 20 h / 140 °C
View Scheme
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; toluene; hexane / -75 - -65 °C / Inert atmosphere
1.2: -75 - -70 °C
1.3: 12 h / -75 - 30 °C
2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
1.2: 3 h / 20 °C
2.1: triethylsilane; boron trifluoride diethyl etherate / chloroform / 3 h / -40 - 20 °C / Inert atmosphere
3.1: palladium 10% on activated carbon / dichloromethane / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: n-butyllithium / toluene / -18 - -5 °C
2: methanol / 0 - 20 °C
3: acetonitrile boron trifluoride complex; triethylsilane / n-heptane / 5 h / -5 - 5 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sodium iodide; copper(l) iodide; N,N`-dimethylethylenediamine / toluene; diethylene glycol dimethyl ether / 36 h / Inert atmosphere; Reflux
2.1: tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
2.2: 2 h / 0 - 5 °C
2.3: 2 h / Cooling
3.1: 4-methyl-morpholine; dmap / toluene; ethyl acetate / 15 h / 0 - 20 °C
4.1: triethylsilane; boron trifluoride diethyl etherate / acetonitrile / 4 h / 0 °C
5.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 19.5 h / 20 - 24 °C
View Scheme
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

bis(3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl)chloroalane

bis(3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl)chloroalane

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In hexane; di-isopropyl ether; toluene at 0℃; Inert atmosphere; Schlenk technique;
Stage #2: With aluminum (III) chloride In hexane; di-isopropyl ether; dibutyl ether; toluene at 90℃; Inert atmosphere; Schlenk technique;
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

3,4,6-tri-O-benzyl-D-glucal epoxide
74372-90-0

3,4,6-tri-O-benzyl-D-glucal epoxide

A

C45H43FO5S

C45H43FO5S

B

(2S,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3-ol

(2S,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3-ol

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With tri-n-butyllithium magnesate complex In tetrahydrofuran; diethyl ether; hexane at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: With copper(I) cyanide di(lithium chloride) In tetrahydrofuran; diethyl ether; hexane at 0℃; for 0.5h; Inert atmosphere;
Stage #3: 3,4,6-tri-O-benzyl-D-glucal epoxide In tetrahydrofuran; diethyl ether; hexane at 0 - 20℃; Inert atmosphere;

1030825-20-7Relevant articles and documents

METHOD FOR PRODUCING 5-BROMO-2-ALKYLBENZOIC ACID

-

Paragraph 0068; 0072-0074, (2021/09/03)

PROBLEM TO BE SOLVED: To provide a method for producing 5-bromo-2-alkylbenzoic acid, which is useful as a synthetic intermediate of a drug substance such as an antidiabetic, in an industrially inexpensive and efficient manner. SOLUTION: The present disclosure provides a method for producing 5-bromo-2-alkylbenzoic acid by bringing 2-alkylbenzoic acid and bromine into contact with each other, in the presence of sulfuric acid. Particularly if 2-alkylbenzoic acid is 2-methylbenzoic acid, the inventive production method enables efficient production of 5-bromo-2-methylbenzoic acid to be a raw material for producing canagliflozin, one of antidiabetics. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Preparation method of 2-(4-fluorophenyl)-5-[(5-bromo-2-methylphenyl)methyl]thiophene

-

, (2020/04/17)

The invention belongs to the field of chemistry, and particularly relates to a novel synthesis method of a key intermediate 2-(4-fluorophenyl)-5-[(5-bromo-2-methylphenyl)methyl]thiophene for preparinga medicine canagliflozin for treating type 2 diabetes mellitus. Cheap and easily available 2-methylthiophene used as an initial raw material undergoes five steps of halogenation, p-nitrotoluene alkylation, coupling, nitro reduction and a Sandmeyer reaction to prepare the product. The method has the characteristics of simplicity in operation, high reaction selectivity, few byproducts and high product quality.

Preparation method for canagliflozin intermediate

-

, (2020/03/09)

The invention relates to a preparation method for a canagliflozin intermediate. The canagliflozin key intermediate, namely 2-(4-fluorophenyl)-5-[(5-bromo-2-methylphenyl)methyl]thiophene is obtained through a three-step reaction of coupling, N-halogenated succinimide halogenation and p-bromotoluene alkylation by using easily-available 2-bromo-5-methylthiophene as a starting raw material. The preparation method provided by the invention has the characteristics of easily-available raw materials, short production steps, simple operation, stable process, high yield and good product quality.

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