Boron tribromide → 1-(3-Hydroxyphenyl)cyclobutane-1-carbonitrile
Reaction equation
[C:1]([C:3]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13]C)[CH:8]=2)[CH2:6][CH2:5][CH2:4]1)#[N:2].B(Br)(Br)Br>ClCCl>[C:1]([C:3]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=2)[CH2:6][CH2:5][CH2:4]1)#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1-cyano-1-(3-methoxyphenyl)cyclobutane (1.93 g, 10 mmol) in dry dichloromethane (50 ml) was added a 1.0M solution of boron tribromide in dichloromethane (22 ml, 22 mmol) at 0° C. and the mixture stirred for 30 min at the same temperature, then overnight at room temperature. The reaction mixture was quenched by the addition of water (100 ml) and extracted with dichloromethane (50 ml×2). The organic phase was washed with brine (50 ml), dried (MgSO4) and concentrated in vacuo to afford 1.70 g (100%) of the titled compound as a clear brown oil.
Workup
- customovernight
- customat room temperature
- customThe reaction mixture was quenched by the addition of water (100 ml)
- extractionextracted with dichloromethane (50 ml×2)
- washThe organic phase was washed with brine (50 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-34b0babcdd864886bae2c5a235d69bf3
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05883106
Reaction notes
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