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1030825-20-7

Basic Information
CAS No.: 1030825-20-7
Name: 2-(5-Bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiophene
Molecular Structure:
Molecular Structure of 1030825-20-7 (2-(5-Bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiophene)
Formula: C18H14BrFS
Molecular Weight: 361.27100
Synonyms: Thiophene, 2-[(5-bromo-2-methylphenyl)methyl]-5-(4-fluorophenyl)-;
EINECS: 807-103-7
Density: 1.388
Melting Point: 103 °C
Boiling Point: 438.3±40.0 °C(Predicted)
Flash Point:
Solubility:
Appearance:
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 28.24000
LogP: 6.21590
Synthetic route
1132832-75-7

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

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%
106-38-7

para-bromotoluene

2-chloromethyl-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

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

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%
58861-48-6

2-(4-fluorophenyl)thiophene

87604-18-0

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

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%
106-38-7

para-bromotoluene

2-bromomethyl-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%
460-00-4

1-Bromo-4-fluorobenzene

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
58861-48-6

2-(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
21900-41-4

5-bromo-2-methylbenzoyl chloride

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
79669-49-1

5-bromo-2-methylbenzoic acid

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
115933-30-7

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

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
918487-45-3

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

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
98-03-3

thiophene-2-carbaldehyde

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
249504-38-9

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

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
1765-93-1

4-fluoroboronic acid

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
64688-68-2

2-methyl-5-nitrobenzoyl chloride

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

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
90050-59-2

5-bromo-2-methylbenzaldehyde

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
462-06-6

fluorobenzene

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
366-77-8

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

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
4701-17-1

5-bromo-2-thiophencarboxaldehyde

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
1225916-69-7

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

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

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
14594-25-3

ethyl 5-bromo-4-oxopentanoate

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
106-38-7

para-bromotoluene

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
765-58-2

2-bromo-5-methyl 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
554-14-3

2-Methylthiophene

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
59311-27-2

2-bromo-5-(bromomethyl)-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

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
58861-48-6

2-(4-fluorophenyl)thiophene

79669-49-1

5-bromo-2-methylbenzoic acid

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
13096-62-3

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

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

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%
1030825-20-7

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

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

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;
67-56-1

methanol

1030825-20-7

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

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

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;
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)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%
67-56-1

methanol

1030825-20-7

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

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

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%
1030825-20-7

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

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

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%
1030825-20-7

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

C70H82O6Si4

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%
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

(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%
75-75-2

methanesulfonic acid

1030825-20-7

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

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

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%
1030825-20-7

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

C18H42O6Si4

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%
1030825-20-7

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

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

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%
1030825-20-7

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

1432591-75-7

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

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%
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

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%
1030825-20-7

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

73852-19-4

3,5-bis-trifluromethylphenylboronic acid

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%
1030825-20-7

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

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

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

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;
1030825-20-7

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

110391-10-1

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

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
1030825-20-7

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

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
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

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;
1030825-20-7

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

74372-90-0

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

A

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

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;
Downstream Products
898566-17-1
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    2-(5-BroMo-2-Methylbenzyl)-5-(4-fluorophenyl)thiophene

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Specification

The 2-(5-Bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiophene, with the CAS registry number 1030825-20-7, is also known Thiophene,2-[(5-bromo-2-methylphenyl)methyl]-5-(4-fluorophenyl)-.This chemical's molecular formula is C18H14BrFS and molecular weight is 361.27 .It belongs to the product Organic matters.What's more,Its systematic name is 2-(5-Bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiophene.

Physical properties about 2-(5-Bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiophene are: (1)ACD/LogP: 6.93±0.52; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.94; (4)ACD/LogD (pH 7.4): 6.94; (5)ACD/BCF (pH 5.5): 109720.70; (6)ACD/BCF (pH 7.4): 109720.70; (7)ACD/KOC (pH 5.5): 141064.20; (8)ACD/KOC (pH 7.4): 141064.20; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.617; (13)Molar Refractivity: 91.1±0.3 cm3; (14)Molar Volume: 260.3±3.0 cm3; (15)Polarizability: 36.1±0.5 10-24cm3; (16)Surface Tension: 43.9±3.0 dyne/cm; (17)Density: 1.4±0.1 g/cm3 ; (18)Flash Point: 218.9±27.3 °C; (19)Enthalpy of Vaporization: 66.8±3.0 kJ/mol; (20)Boiling Point: 438.3±40.0 °C at 760 mmHg; (21)Vapour Pressure: 0.0±1.0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:Cc1ccc(cc1Cc2ccc(s2)c3ccc(cc3)F)Br;
(2)Std. 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;
(3)Std. InChIKey:VLRIERSBZHUCOW-UHFFFAOYSA-N.