Methanol → Benzeneethanol, 3-(bromomethyl)-
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- stirringstirred overnight
- concentrationthe mixture concentrated in vacuo
- customPurification
- 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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