Réaction #6022

Équation de réaction

4-bromomethylbenzoic acid

borane THF

→

title compound

Rendement 94.8%

4-(bromomethyl)benzylalcohol

Rendement 94.8%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreThe ice bath was removed
2. 2
   Températureto warm to room temperature
3. 3
   AutreThe 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
   Lavagewashed with 4% HCl, water NaHCO3, brine
7. 7
   Séchagedried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated in vacuo

Mode opératoire

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