Methanol → Benzeneethanol, 3-(bromomethyl)-

HRID 1689205Notes

Reaction equation

HRID 1689205 reaction equation
CSC.B.[Br:5][CH2:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14](O)=[O:15])[CH:10]=[CH:11][CH:12]=1.CO>C1COCC1>[Br:5][CH2:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][OH:15])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 103765092-(3-(Bromomethyl)phenyl)acetic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 18999576Benzeneethanol, 3-(bromomethyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane dimethylsulphide complex (2M solution in THF, 5.78 mL) was added dropwise to a solution of 2-(3-(bromomethyl)phenyl)acetic acid (1.06 g) in THF (10 mL) at 0° C. and the resulting mixture stirred for 10 min. The reaction was then allowed to warm to room temperature and stirred overnight. Methanol (5 mL) was then added and the mixture concentrated in vacuo. Purification was by silica gel chromatography eluting with isohexane to diethyl ether gradient to give the subtitled compound as a white solid. Yield 1 g.

Workup

  1. stirringstirred overnight
  2. concentrationthe mixture concentrated in vacuo
  3. customPurification
  4. washeluting with isohexane to diethyl ether gradient

Sources & evidence

ORD record
ord-4d1cfd67816a48ee9430ad7760b41a50
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

Loading…