Methanol → Benzeneethanol, 3-(bromomethyl)-

HRID 470974Notes

Reaction equation

HRID 470974 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-2ad67469a81d4a00a5fbada5e063f898
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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