4-(Bromomethyl)benzoic acid → 4-(Bromomethyl)benzyl alcohol

Temperature

0 °C

A suspension of 4-bromomethylbenzoic acid (5.04 g, 23.3 mmol) in THF (30 mL) was cooled to 0° C. and treated with borane/THF (35 mmol). The ice bath was removed and the mixture was allowed to warm to room temperature and stirred for 1.5 hours. The excess borane was quenched first with MeOH, then with water. The reaction mixture was then concentrated in vacuo and redissolved in ethyl acetate. The ethyl acetate layer was washed with 5% HCl, water, NaHCO3, brine, dried (MgSO4), filtered, and evaporated in vacuo to afford 4.44 g (94%) of the titled product.

1. customThe ice bath was removed
2. temperatureto warm to room temperature
3. customThe excess borane was quenched first with MeOH
4. concentrationThe reaction mixture was then concentrated in vacuo
5. dissolutionredissolved in ethyl acetate
6. washThe ethyl acetate layer was washed with 5% HCl, water, NaHCO3, brine
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. customevaporated in vacuo

ORD record

ord-df1c2319fdc24a2f9b0756181c5ff34d

Source dataset

uspto-grants-1995_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05449682