Thionyl Chloride → 1-Bromo-3-[chloro(4-chlorophenyl)methyl]benzene

HRID 845218Notes

Reaction equation

HRID 845218 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH:5](O)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.S(Cl)([Cl:19])=O>C(Cl)Cl.N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH:5]([Cl:19])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 53634461HCID 53634461, compound

Product 1

HCID 201324411-Bromo-3-[chloro(4-chlorophenyl)methyl]benzeneYield 103%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of the above benzhydryl alcohol (13.0 g, 43 mmol) in 100 mL of methylene chloride and 5 mL of pyridine was stirred at room temperature during dropwise addition of 4.7 mL (64 mmol) of thionyl chloride in 20 mL of methylene chloride. After stirring overnight, the reaction solution was washed with two 60 mL portions of 1M hydrochloric acid and 50 mL of water and dried over magnesium sulfate. Evaporation of the solvent gave 14.0 g of 3-bromo-4'-chlorobenzhydryl chloride as a pale yellow oil. A portion was purified by chromatography on silica gel with hexane to give a colorless oil. Calc. for C13H9BrCl2 : C, 49.41; H, 2,87; Br, 25.28; Cl, 22.44. Found: C, 49.50; H, 2.82; Br, 25.27; Cl, 22.48.

Workup

  1. washthe reaction solution was washed with two 60 mL portions of 1M hydrochloric acid and 50 mL of water
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-924710593a034fc1b7fde553d7d12ba3
Source dataset
uspto-grants-1988_07
Patent number
US04757074

Reaction notes

Loading…