Boron tribromide → HCID 58907430, compound
Reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH2:10][C:11]#[N:12])=[C:5]([CH3:13])[CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH2:10][C:11]#[N:12])=[C:5]([CH3:13])[CH:4]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -80 °C
Procedure
A solution of (4-methoxy-2,5-dimethylphenyl)acetonitrile (0.5 g, 2.9 mmol) in dichloromethane (10 ml) was cooled to −80° C. and treated with a solution of boron tribromide in dichloromethane (14.3 ml of a 1M solution, 14.3 mmol). The reaction mixture was stirred at −80° C. for a further 30 minutes and then gradually allowed to warm to room temperature over a period of 2 hours. The reaction mixture was quenched with saturated aqueous sodium bicarbonate (20 ml) and the organic phase separated. The organic phase was washed with saturated aqueous sodium chloride (20 ml), dried (sodium sulfate) and the solvent removed in vacuo to give a pale brown solid. Purification by column chromatography on silica gel eluting with ethyl acetate:pentane (1:4 changing to 1:2) gave the title compound as a colourless solid (0.28 g).
Workup
- temperatureto warm to room temperature over a period of 2 hours
- customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate (20 ml)
- customthe organic phase separated
- washThe organic phase was washed with saturated aqueous sodium chloride (20 ml)
- dry with materialdried (sodium sulfate)
- customthe solvent removed in vacuo
- customto give a pale brown solid
- customPurification by column chromatography on silica gel eluting with ethyl acetate:pentane (1:4 changing to 1:2)
Sources & evidence
- ORD record
- ord-f5d073133f1c49b6b721843606a626b4
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08013019B2
Reaction notes
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