4-Bromo-2-methylbenzoic acid → (4-Bromo-2-methylphenyl)methanol

Temperature

0 °C

4-Bromo-2-methyl-benzoic acid (9.88 g, 45.9 mmol) was dissolved in THF (100 ml), and the solution was cooled to 0° C. To this solution, a solution of 1M BH3.THF (91.89 ml, 91.89 mmol) was added at 0° C., and the solution was vigorously stirred for 3 hours at room temperature. The reaction mixture was diluted with cold water (20 mL), washed with a saturated solution of NaHCO3, then extracted with ether 3 times (300 mL). The combined organic ether was washed with brine (250 mL), dried over MgSO4, and concentrated in Vacuo. The residue was purified via flash column chromatography (25% to 55% EtOAc in Hexane) to give white solid (8.24 g, 90% yield). 1H NMR (400 MHz, CDCl3) δ: 2.32 (2 H, s) 4.64 (1 H, d, J=5.81 Hz) 7.20-7.26 (2 H, m) 7.30-7.36 (1 H, m).

1. washwashed with a saturated solution of NaHCO3
2. extractionextracted with ether 3 times (300 mL)
3. washThe combined organic ether was washed with brine (250 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated in Vacuo
6. customThe residue was purified via flash column chromatography (25% to 55% EtOAc in Hexane)

ORD record

ord-c75f21b394e142aca07357bb7e1d4ee2

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268835B2