Hydrochloric Acid → (5-Bromo-2-chlorophenyl)methanol

10 g (42.5 mmol) of 5-bromo-3-chlorobenzoic acid are dissolved in 135 ml of THF. At 0° C., 4.2 g (55.2 mmol, 5.24 ml) of borane-dimethyl sulfide complex are added dropwise. The mixture is then stirred at RT for 25 min and under reflux for 30 min. 40 ml of water and 15 ml of 2N hydrochloric acid are successively added dropwise while cooling in ice, followed by stirring at RT for 45 min. After a renewed addition of 15 ml of 2N hydrochloric acid the mixture is extracted several times with diethyl ether. The combined organic phase is washed successively with 1N hydrochloric acid, water, a saturated sodium bicarbonate solution and a saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo. The solid is dried under high vacuum to constant weight.

1. additionAt 0° C., 4.2 g (55.2 mmol, 5.24 ml) of borane-dimethyl sulfide complex are added dropwise
2. temperatureunder reflux for 30 min
3. temperaturewhile cooling in ice
4. stirringby stirring at RT for 45 min
5. extractionis extracted several times with diethyl ether
6. washThe combined organic phase is washed successively with 1N hydrochloric acid, water
7. dry with materiala saturated sodium bicarbonate solution and a saturated sodium chloride solution, dried over magnesium sulfate
8. concentrationconcentrated in vacuo
9. customThe solid is dried under high vacuum to constant weight

ORD record

ord-a26ce59230f340099cd09c773006b517

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07655643B2