Benzene → 2-(4-Bromophenyl)ethane-1-sulfonyl chloride

Thionyl chloride (1.51 mL, 20.8 mmol) was added dropwise at 0° C. to a suspension of sodium 2-(4-bromo-phenyl)-ethanesulfonate (4.33 g, 15.08 mmol) in a mixture of anhydrous benzene (50 mL) and N,N-dimethylformamide (1 mL). The reaction mixture was allowed to warm to room temperature and was then heated at 80° C. for 18 hours. The reaction mixture was cooled to room temperature and filtered through a pad of Celite. The solids were washed with benzene and the combined filtrates were concentrated in vacuo. The residue was taken up in hexane (30 mL) and the resulting suspension was heated at 50° C. for 30 min. After cooling to room temperature, the formed precipitate was collected by filtration to give 4.06 g (95% yield) of the title compound.

1. temperaturewas then heated at 80° C. for 18 hours
2. temperatureThe reaction mixture was cooled to room temperature
3. filtrationfiltered through a pad of Celite
4. washThe solids were washed with benzene
5. concentrationthe combined filtrates were concentrated in vacuo
6. temperaturethe resulting suspension was heated at 50° C. for 30 min
7. temperatureAfter cooling to room temperature
8. filtrationthe formed precipitate was collected by filtration

ORD record

ord-cf4fda9edebf415cafa6f10b6480e130

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09145380B2