Bromine → 2-Bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethan-1-one

A solution of bromine (10.2 ml) in dichloromethane (50 ml) was added dropwise over 3.5 hours at 10-15° C. under nitrogen to a stirred solution of 1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone (47 g) in a mixture of methanol (75 ml) and dichloromethane (15 ml). After the addition was complete, the mixture was stirred at ambient temperature for 2.5 hours, then poured onto ice-water (500 ml). The aqueous layer was separated and washed with dichloromethane (3×100 ml), then the combined organic solutions were washed with saturated aqueous sodium hydrogen carbonate solution (2×100 ml) and water (100 ml), dried (CaCl2), and the solvents removed in vacua. The residue was distilled to give 2-bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone as a pale yellow oil (40.2 g), b.p. 156-164° C. at 0.8 mbar.

1. additionAfter the addition
2. additionpoured onto ice-water (500 ml)
3. customThe aqueous layer was separated
4. washwashed with dichloromethane (3×100 ml)
5. washthe combined organic solutions were washed with saturated aqueous sodium hydrogen carbonate solution (2×100 ml) and water (100 ml)
6. dry with materialdried (CaCl2)
7. customthe solvents removed in vacua
8. distillationThe residue was distilled

ORD record

ord-b0017fb5fc604152bc8c7bc341ff7150

Source dataset

uspto-grants-2001_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06187802B1