Water → 3-(3-Bromo-4-fluorophenyl)propanenitrile
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+].O>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[F:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of (E)-3-(3-bromo-4-fluorophenyl)acrylonitrile (35.0 g, 108 mmol) in ethanol (20 mL) at 0° C. was added sodium tetrahydroborate (16.40 g, 434 mmol). The reaction mixture was allowed to warm to 70° C. and stirred for 4 h. Water was added to quench the reaction, and the organic layer was separated. The water layer was extracted with DCM twice, and the combined organic phase was dried and concentrated. The residue was purified by chromatography to afford the title compound as an oil (20 g, 64.7% yield). LCMS: rt=1.45 min, [M+H+]=228
Workup
- customto quench
- customthe reaction
- customthe organic layer was separated
- extractionThe water layer was extracted with DCM twice
- customthe combined organic phase was dried
- concentrationconcentrated
- customThe residue was purified by chromatography
Sources & evidence
- ORD record
- ord-7bae86022e174a06989fd226a8c83e4e
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174968B2
Reaction notes
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