Boron tribromide → 2-Chloro-4-methyl-quinolin-6-ol

A solution of 2-chloro-6-methoxy-4-methylquinoline (0.20 g) in dichloromethane (15 mL) was cooled to −78° C., followed by addition of a solution (5.3 mL) of 1 M boron tribromide in dichloromethane, and the mixture was stirred for 12 h while slowly heating to room temperature. To the reaction mixture was added a saturated sodium hydrogencarbonate solution to make it basic, and the mixture was extracted with chloroform. The aqueous layer was reextracted with a mixture solution of ethyl acetate and n-butanol, then the organic layer was combined and concentrated under reduced pressure, and the resulting solids were washed with diethyl ether to obtain 2-chloro-6-hydroxy-4-methylquinoline (0.15 g).

1. extractionthe mixture was extracted with chloroform
2. concentrationconcentrated under reduced pressure
3. washthe resulting solids were washed with diethyl ether

ORD record

ord-a3f835033b6041bb9711c03341fcb6e9

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08044068B2