Water → 2-Bromo-2,6-dichloro-6-fluorocyclohexanol

2.91 cm3 (2.91 mmol) of BBr3 in molar solution in dichloromethane were introduced at 4° C. under argon atmosphere into 0.98 (5.3 mmol) of epoxide 2e in solution in 6.5 cm3 dichloromethane. The reaction mixture was then allowed to return to room temperature and stirring was continued (1 h 30 min). 5 cm3 of distilled water were then added and the mixture was extracted with dichloromethane (4×10 cm3). The extract was dried over MgSO4, filtered and evaporated down. The crude product was purified by flash chromatography on silica (eluent ether/petroleum ether=5/95): 1.03 g of alcohol 1i were obtained (macrobore GC purity>97%); the yield of product 1i was 73%.

1. customto return to room temperature
2. custom(1 h 30 min)
3. extractionthe mixture was extracted with dichloromethane (4×10 cm3)
4. dry with materialThe extract was dried over MgSO4
5. filtrationfiltered
6. customevaporated down
7. customThe crude product was purified by flash chromatography on silica (eluent ether/petroleum ether=5/95)

ORD record

ord-a254a47f4a7b42b890ab20256a72c77c

Source dataset

uspto-grants-1995_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05424460