Water → (4-Bromo-2-methylphenyl)methanol

Temperature

2.5 °C

4-Bromo-2-methylbenzoic acid (11.1 g, 51.6 mmol) is dissolved in anhydrous THF (11.2 mL). The solution is cooled to 0-5° C. and a 1 M solution of BH3. THF (103 mL) is added to the mixture. The solution is left stirring 3 h at room temperature. Cold water is then added (20 mL) and the reaction mixture is washed with a saturated solution of NaHCO3 (120 mL). The aqueous phase is extracted with diethyl ether (3×300 mL) and the combined organic phases washed with brine (200 mL), dried with MgSO4 and concentrated in vacuo. The resulting oil is purified by flash-chromatography, eluting with hexane/EtOAc from 95:5 to 70:30, to provide the expected product (4-Bromo-2-methylphenyl)methanol (10.4 g, 100%) as a clear oil.

1. waitThe solution is left
2. washthe reaction mixture is washed with a saturated solution of NaHCO3 (120 mL)
3. extractionThe aqueous phase is extracted with diethyl ether (3×300 mL)
4. washthe combined organic phases washed with brine (200 mL)
5. dry with materialdried with MgSO4
6. concentrationconcentrated in vacuo
7. customThe resulting oil is purified by flash-chromatography
8. washeluting with hexane/EtOAc from 95:5 to 70:30

ORD record

ord-146a210b5b6648d3ade3c9e409fbefb1

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093402B2