Reaction #6022

Reaction equation

4-bromomethylbenzoic acid

borane THF

→

title compound

Yield 94.8%

4-(bromomethyl)benzylalcohol

Yield 94.8%

Solvents

THF

Conditions

Workup

1. 1
   OtherThe ice bath was removed
2. 2
   Temperatureto warm to room temperature
3. 3
   OtherThe excess borane was quenched with MeOH
4. 4
   Concentrationwith water, and the reaction mixture was concentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
6. 6
   Washwashed with 4% HCl, water NaHCO3, brine
7. 7
   Dryingdried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated in vacuo

Procedure

A suspension of 4-bromomethylbenzoic acid (5.04; 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 with MeOH, and then with water, and the reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with 4% HCl, water NaHCO3, brine, dried (MgSO4), filtered, concentrated in vacuo to afford 4.44 g (94%) of the title compound.

Source