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

Temperature

0 °C

4-bromo-2-methylbenzoic acid (5 g, 22.8 mmol) is dissolved in dry THF (100 ml) and cooled to 0° C. A 1M solution of BH3.THF in THF (34 mL, 34 mmol) is slowly added. The resulting colorless suspension is then stirred overnight, allowing it to gradually reach room temperature. K2CO3 solid (1.1 g) and H2O (100 ml) are added to the colorless solution and the mixture is stirred for an additional 30 minutes. THF is then evaporated and the residue extracted with EtOAc (30 ml). The organic phase is washed with 1N HCl (3×50 ml), dried over Na2SO4 and evaporated. The residue gives the title compound which is used in the next step without further purification.

1. customto gradually reach room temperature
2. stirringthe mixture is stirred for an additional 30 minutes
3. customTHF is then evaporated
4. extractionthe residue extracted with EtOAc (30 ml)
5. washThe organic phase is washed with 1N HCl (3×50 ml)
6. dry with materialdried over Na2SO4
7. customevaporated

ORD record

ord-2927d44e4cc7498981c270d342fcb46c

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08193189B2