Thionyl Chloride → 4-Bromo-1-chloro-2-(chloromethyl)benzene

Temperature

100 °C

To a solution of 5-bromo-2-chlorobenzyl alcohol (10.66 g) in toluene (100 ml) solution were added thionyl chloride (10 ml), and pyridine (2 drops), and the mixture was stirred under heating at 100° C. overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was washed successively with water, a 10% aqueous hydrochloric acid solution, a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give 5-bromo-2-chlorobenzyl chloride as pale yellow crystals, which was used in the subsequent step without further purification.

1. customThe solvent was evaporated under reduced pressure
2. dissolutionthe residue was dissolved in ethyl acetate
3. washThe solution was washed successively with water
4. dry with materiala 10% aqueous hydrochloric acid solution, a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over sodium sulfate
5. customThe solvent was evaporated under reduced pressure

ORD record

ord-4d69de89a4eb4b4cb53d107fa858b582

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785403B2