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1261817-10-0

2-Iodo-5-BromoBenzyl chloride is a chemical compound that is a derivative of benzyl chloride, featuring the addition of iodine and bromine atoms. It is recognized for its reactivity in various chemical reactions, such as nucleophilic substitution and metal-catalyzed cross-coupling, and is valued for its versatility in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. 2-Iodo-5-BroMobenzyl chloride serves as a valuable building block for creating compounds with diverse biological activities.

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  • 1261817-10-0 Structure

  • Basic information

    1. Product Name: 2-Iodo-5-BroMobenzyl chloride
    2. Synonyms: 4-Bromo-2-(chloromethyl)-1-iodobenzene;2-Iodo-5-BroMobenzyl chloride;5-bromo-2-iodobenzyl chloride
    3. CAS NO:1261817-10-0
    4. Molecular Formula: C7H5BrClI
    5. Molecular Weight: 331.37607
    6. EINECS: -0
    7. Product Categories: N/A
    8. Mol File: 1261817-10-0.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 324.0±27.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 2.132±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 2-Iodo-5-BroMobenzyl chloride(CAS DataBase Reference)
    10. NIST Chemistry Reference: 2-Iodo-5-BroMobenzyl chloride(1261817-10-0)
    11. EPA Substance Registry System: 2-Iodo-5-BroMobenzyl chloride(1261817-10-0)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1261817-10-0(Hazardous Substances Data)

1261817-10-0 Usage

Uses

Used in Organic Synthesis:
2-Iodo-5-BromoBenzyl chloride is used as a reactive substrate in organic synthesis for its ability to participate in nucleophilic substitution and metal-catalyzed cross-coupling reactions, facilitating the creation of a wide range of chemical products.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-Iodo-5-BromoBenzyl chloride is utilized as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs with potential therapeutic applications.
Used in the Production of Agrochemicals:
2-Iodo-5-BromoBenzyl chloride is employed as a building block in the agrochemical industry, aiding in the synthesis of compounds with pesticidal or herbicidal properties, thereby enhancing crop protection and yield.
Used in the Synthesis of Fine Chemicals:
2-Iodo-5-BroMobenzyl chloride is also used in the synthesis of fine chemicals, where its unique properties allow for the creation of specialty chemicals used in various industries, such as fragrances, dyes, and coatings.
Used in the Development of Compounds with Biological Activities:
2-Iodo-5-BromoBenzyl chloride serves as a valuable precursor in the development of compounds that exhibit biological activities, potentially leading to new treatments and therapeutic agents in medicine and biotechnology.

Check Digit Verification of cas no

The CAS Registry Mumber 1261817-10-0 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,2,6,1,8,1 and 7 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 1261817-10:
(9*1)+(8*2)+(7*6)+(6*1)+(5*8)+(4*1)+(3*7)+(2*1)+(1*0)=140
140 % 10 = 0
So 1261817-10-0 is a valid CAS Registry Number.

1261817-10-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-bromo-2-(chloromethyl)-1-iodobenzene

1.2 Other means of identification

Product number -
Other names 2-Iodo-5-Bromobenzyl chloride

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:1261817-10-0 SDS

1261817-10-0Synthetic route

(5-bromo-2-iodo-phenyl)-methanol
199786-58-8

(5-bromo-2-iodo-phenyl)-methanol

4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

Conditions
ConditionsYield
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 1h;
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

tert-butyl 5'-bromo-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate
1398609-80-7

tert-butyl 5'-bromo-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate

Conditions
ConditionsYield
Stage #1: 4-bromo-2-(chloromethyl)-1-iodobenzene With TurboGrignard In tetrahydrofuran at -40 - -33℃; for 1.5h; Inert atmosphere;
Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran at -40 - 20℃; for 18h;		85.2%
Stage #1: 4-bromo-2-(chloromethyl)-1-iodobenzene With TurboGrignard In tetrahydrofuran at -20 - -15℃;
Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran at -20 - 20℃;		290 g
Stage #1: 4-bromo-2-(chloromethyl)-1-iodobenzene With C4H9ClMg*LiCI In tetrahydrofuran at -20 - -15℃;
Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran at -20 - 20℃;		290 g
With TurboGrignard In tetrahydrofuran at -20 - 20℃;290 g
Stage #1: 4-bromo-2-(chloromethyl)-1-iodobenzene With TurboGrignard In tetrahydrofuran at -15℃; for 0.583333h;
Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran at -30 - 20℃;		1.6 g
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

phenyl 3-oxoazetidine-1-carboxylate

phenyl 3-oxoazetidine-1-carboxylate

phenyl 6-bromospiro[1H-isobenzofuran-3,3'-azetidine]-1'-carboxylate

phenyl 6-bromospiro[1H-isobenzofuran-3,3'-azetidine]-1'-carboxylate

Conditions
ConditionsYield
Stage #1: 4-bromo-2-(chloromethyl)-1-iodobenzene With TurboGrignard In tetrahydrofuran at -35 - -25℃; for 1.5h; Large scale;
Stage #2: phenyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran at -25 - 35℃; for 19h; Temperature; Large scale;		77%
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

2,2,-dimethyl-1,3-dioxan-5-one
74181-34-3

2,2,-dimethyl-1,3-dioxan-5-one

6'-bromo-2,2-dimethyl-spiro[1,3-dioxane-5,3'-1H-isobenzofuran]

6'-bromo-2,2-dimethyl-spiro[1,3-dioxane-5,3'-1H-isobenzofuran]

Conditions
ConditionsYield
Stage #1: 4-bromo-2-(chloromethyl)-1-iodobenzene With TurboGrignard In tetrahydrofuran at -35℃; for 1.5h;
Stage #2: 2,2,-dimethyl-1,3-dioxan-5-one In tetrahydrofuran at -35 - 20℃; Inert atmosphere;		72%
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

1-(3,3,3-trifluoropropanoyl)azetidin-3-one

1-(3,3,3-trifluoropropanoyl)azetidin-3-one

1-(6-bromospiro[1H-isobenzofuran-3,3'-azetidine]-1'-yl)-3,3,3-trifluoropropan-1-one

1-(6-bromospiro[1H-isobenzofuran-3,3'-azetidine]-1'-yl)-3,3,3-trifluoropropan-1-one

Conditions
ConditionsYield
Stage #1: 1-(3,3,3-trifluoropropanoyl)azetidin-3-one With lanthanium (III) chloride bis(lithium chloride) complex In tetrahydrofuran for 2.5h;
Stage #2: 4-bromo-2-(chloromethyl)-1-iodobenzene With TurboGrignard In tetrahydrofuran at -20 - 20℃; for 21h; Reagent/catalyst; Temperature;		71%
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

tert-butyl 5'-acetyl-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate
1398609-81-8

tert-butyl 5'-acetyl-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: TurboGrignard / tetrahydrofuran / -20 - -15 °C
1.2: -20 - 20 °C
2.1: triethylamine; palladium diacetate; 1,3-bis-(diphenylphosphino)propane / ethanol / 0.08 h / 90 °C / Inert atmosphere
2.2: 4 h / 90 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: C4H9ClMg*LiCI / tetrahydrofuran / -20 - -15 °C
1.2: -20 - 20 °C
2.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; triethylamine / ethanol / 4 h / 90 °C / Inert atmosphere
2.2: 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: TurboGrignard / tetrahydrofuran / 0.58 h / -15 °C
1.2: -30 - 20 °C
2.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; triethylamine / ethanol / 0.08 h / 90 °C / Inert atmosphere
2.2: 4 h / 90 °C / Inert atmosphere
2.3: 2 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: TurboGrignard / tetrahydrofuran / 1.5 h / -40 - -33 °C / Inert atmosphere
1.2: 18 h / -40 - 20 °C
2.1: 1,3-bis-(diphenylphosphino)propane; triethylamine / ethanol / 96 °C / Inert atmosphere; Sealed tube
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

tert-butyl 6-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]spiro[1H-isobenzofuran-3,3'-azetidine]-1'-carboxylate
1398610-04-2

tert-butyl 6-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]spiro[1H-isobenzofuran-3,3'-azetidine]-1'-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: TurboGrignard / tetrahydrofuran / -20 - -15 °C
1.2: -20 - 20 °C
2.1: triethylamine; palladium diacetate; 1,3-bis-(diphenylphosphino)propane / ethanol / 0.08 h / 90 °C / Inert atmosphere
2.2: 4 h / 90 °C / Inert atmosphere
3.1: caesium carbonate / toluene / 2 h / 110 °C / Inert atmosphere; Dean-Stark
View Scheme
Multi-step reaction with 3 steps
1.1: C4H9ClMg*LiCI / tetrahydrofuran / -20 - -15 °C
1.2: -20 - 20 °C
2.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; triethylamine / ethanol / 4 h / 90 °C / Inert atmosphere
2.2: 2 h / 20 °C
3.1: α,α,α-trifluorotoluene; caesium carbonate / toluene / 2 h / 110 °C / Dean-Stark; Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3: caesium carbonate / toluene / 16 h / 110 °C
View Scheme
Multi-step reaction with 3 steps
1.1: TurboGrignard / tetrahydrofuran / 0.58 h / -15 °C
1.2: -30 - 20 °C
2.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; triethylamine / ethanol / 0.08 h / 90 °C / Inert atmosphere
2.2: 4 h / 90 °C / Inert atmosphere
2.3: 2 h / 20 °C / Inert atmosphere
3.1: caesium carbonate / toluene / 6 h / 110 °C / Dean-Stark; Inert atmosphere
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

tert-butyl 5'-[3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]-1-carboxylate
1575810-99-9

tert-butyl 5'-[3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 6 h / Inert atmosphere; Reflux
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

5'-[3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]
1575811-03-8

5'-[3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 6 h / Inert atmosphere; Reflux
3: hydrogenchloride / methanol / 0 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

5'-[3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-1-isobutyryl-3'H-spiro[azetidine-3,1'-[2]benzofuran]
1575794-94-3

5'-[3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-1-isobutyryl-3'H-spiro[azetidine-3,1'-[2]benzofuran]

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 6 h / Inert atmosphere; Reflux
3: hydrogenchloride / methanol / 0 °C
4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

tert-butyl 5'-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]-1-carboxylate
1575811-05-0

tert-butyl 5'-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 6 h / Inert atmosphere; Reflux
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

5'-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]
1575811-07-2

5'-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 6 h / Inert atmosphere; Reflux
3: hydrogenchloride / methanol / 0.25 h / 20 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

5'-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine-1-yl]-1-[(methylsulfonyl)acetyl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]
1575795-00-4

5'-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine-1-yl]-1-[(methylsulfonyl)acetyl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 6 h / Inert atmosphere; Reflux
3: hydrogenchloride / methanol / 0.25 h / 20 °C
4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

5'-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-1-isobutyryl-3'H-spiro[azetidine-3,1'-[2]benzofuran]
1575795-02-6

5'-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-1-isobutyryl-3'H-spiro[azetidine-3,1'-[2]benzofuran]

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 6 h / Inert atmosphere; Reflux
3: hydrogenchloride / methanol / 0.25 h / 20 °C
4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

tert-butyl 5'-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-2-enoyl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate
1575810-06-8

tert-butyl 5'-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-2-enoyl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3: caesium carbonate / toluene / 16 h / 110 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

tert-butyl 5'-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]-1-carboxylate
1575811-10-7

tert-butyl 5'-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 12 h / Inert atmosphere; Reflux
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

5'-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]
1575811-13-0

5'-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 12 h / Inert atmosphere; Reflux
3: hydrogenchloride / methanol / 0.25 h / 20 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

1-isobutyryl-5'-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]
1575795-11-7

1-isobutyryl-5'-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 12 h / Inert atmosphere; Reflux
3: hydrogenchloride / methanol / 0.25 h / 20 °C
4: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / tetrahydrofuran; ethyl acetate / 12 h / 20 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

tert-butyl 5'-(4,4,4-trifluoro-3-(nitromethyl)-3-(3,4,5-trichlorophenyl)butanoyl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate
1575810-08-0

tert-butyl 5'-(4,4,4-trifluoro-3-(nitromethyl)-3-(3,4,5-trichlorophenyl)butanoyl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3: caesium carbonate / toluene / 16 h / 110 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 16 h / 20 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

tert-butyl 5'-(3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate
1575810-11-5

tert-butyl 5'-(3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3: caesium carbonate / toluene / 16 h / 110 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 16 h / 20 °C
5: hydrogen / ethanol; water / 16 h / 20 °C / Inert atmosphere
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

5'-(3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran] hydrochloride
1575810-14-8

5'-(3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran] hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3: caesium carbonate / toluene / 16 h / 110 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 16 h / 20 °C
5: hydrogen / ethanol; water / 16 h / 20 °C / Inert atmosphere
6: hydrogenchloride / methanol / 0.5 h / 0 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

2-(methylsulfonyl)-1-(5'-(3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)ethanone
1575794-22-7

2-(methylsulfonyl)-1-(5'-(3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)ethanone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3: caesium carbonate / toluene / 16 h / 110 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 16 h / 20 °C
5: hydrogen / ethanol; water / 16 h / 20 °C / Inert atmosphere
6: hydrogenchloride / methanol / 0.5 h / 0 °C
7: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / tetrahydrofuran; ethyl acetate / 16 h / 20 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

2-methyl-1-(5'-(3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)propan-1-one
1575794-26-1

2-methyl-1-(5'-(3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)propan-1-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3: caesium carbonate / toluene / 16 h / 110 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 16 h / 20 °C
5: hydrogen / ethanol; water / 16 h / 20 °C / Inert atmosphere
6: hydrogenchloride / methanol / 0.5 h / 0 °C
7: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / tetrahydrofuran; ethyl acetate / 16 h / 20 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

tert-butyl 5'-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-3-(nitromethyl)butanoyl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate
1575810-19-3

tert-butyl 5'-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-3-(nitromethyl)butanoyl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3: caesium carbonate / toluene / 16 h / 110 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 16 h / 20 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

tert-butyl 5'-(3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate
1575810-21-7

tert-butyl 5'-(3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3: caesium carbonate / toluene / 16 h / 110 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 16 h / 20 °C
5: hydrogen / ethanol; water / 16 h / 20 °C / Inert atmosphere
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

5'-(3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran] hydrochloride
1575810-24-0

5'-(3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran] hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3: caesium carbonate / toluene / 16 h / 110 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 16 h / 20 °C
5: hydrogen / ethanol; water / 16 h / 20 °C / Inert atmosphere
6: hydrogenchloride / methanol / 0.5 h / 0 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

1-(5'-(3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-(methylsulfonyl)ethanone
1575794-28-3

1-(5'-(3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-(methylsulfonyl)ethanone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3: caesium carbonate / toluene / 16 h / 110 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 16 h / 20 °C
5: hydrogen / ethanol; water / 16 h / 20 °C / Inert atmosphere
6: hydrogenchloride / methanol / 0.5 h / 0 °C
7: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine / tetrahydrofuran; ethyl acetate / 16 h / 20 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

1-(5'-(3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-methylpropan-1-one
1575794-32-9

1-(5'-(3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-methylpropan-1-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3: caesium carbonate / toluene / 16 h / 110 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 16 h / 20 °C
5: hydrogen / ethanol; water / 16 h / 20 °C / Inert atmosphere
6: hydrogenchloride / methanol / 0.5 h / 0 °C
7: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / tetrahydrofuran / 16 h / 20 °C
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

tert-butyl 5'-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutyryl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]-1-carboxylate
1575810-35-3

tert-butyl 5'-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutyryl]-3'H-spiro[azetidine-3,1'-[2]benzofuran]-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3: triethylamine / n-heptane / 16 h / 60 °C / Sealed tube
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-1-(3'H-spiro[azetidine-3,1'-isobenzofuran]-5'-yl)but-2-en-1-one hydrochloride
1575810-60-4

3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-1-(3'H-spiro[azetidine-3,1'-isobenzofuran]-5'-yl)but-2-en-1-one hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3: caesium carbonate / toluene / 16 h / 110 °C
4: hydrogenchloride / methanol / 0.12 h / 120 °C / Microwave irradiation
View Scheme
4-bromo-2-(chloromethyl)-1-iodobenzene
1261817-10-0

4-bromo-2-(chloromethyl)-1-iodobenzene

3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-1-(1-(2-(methylsulfonyl)acetyl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-5'-yl)but-2-en-1-one
1575810-62-6

3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluoro-1-(1-(2-(methylsulfonyl)acetyl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-5'-yl)but-2-en-1-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: TurboGrignard / tetrahydrofuran / -20 - 20 °C
2.1: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / ethanol / 16 h / 96 °C / Autoclave; Inert atmosphere
3.1: caesium carbonate / toluene / 16 h / 110 °C
4.1: hydrogenchloride / methanol / 0.12 h / 120 °C / Microwave irradiation
5.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 0.5 h
5.2: 6 h / 20 °C
View Scheme

1261817-10-0Relevant articles and documents

Palladium(II)-Catalyzed Annulation of Alkynes with 2-(Cyanomethyl)phenylboronates Leading to 3,4-Disubstituted 2-Naphthalenamines

Tsukamoto, Hirokazu,Ikeda, Taishi,Doi, Takayuki

, p. 1733 - 1745 (2016/03/15)

1,2-Bis(diphenylphosphino)ethane (dppe)-ligated palladium(II) complexes catalyze the annulation of internal alkynes with 2-(cyanomethyl)phenylboronates to provide 3,4-disubstituted-2-naphthalenamines in good yields. The annulation reaction proceeds under mild and neutral conditions and requires methanol as an essential solvent. In addition to symmetrical alkynes, unsymmetrical alkynes substituted by aryl, alkyl, and alkynyl groups participate in the annulation to afford the corresponding 2-naphthalenamines with electron-withdrawing sp2- and sp-carbons preferentially located at the C-3 position. Substituents including an alkyl or alkoxy group on the cyanomethyl moiety and a halogen atom on the benzene ring in the boronates are compatible with the reaction conditions. The annulation proceeds through the transmetalation of the palladium(II) complexes with the boronates and alkyne insertion followed by nucleophilic addition of the generated alkenylpalladium(II) species to the intramolecular cyano group. Stoichiometric reactions revealed that the methanol solvent was effective for both transmetalation and catalyst regeneration.

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