Water → 2-Ethenyl-3-fluorobenzaldehyde
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]=[CH2:10].C([Li])CCC.CN(C)[CH:18]=[O:19].O>C1COCC1>[F:8][C:4]1[C:3]([CH:9]=[CH2:10])=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:18]=[O:19]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 1-bromo-3-fluoro-2-vinylbenzene (900 mg) in THF (40 ml) was added dropwise, at −78° C., n-butyllithium (3.4 ml 1.6 M/hexane). After 60 minutes, N,N-dimethylformamide (0.69 ml) was added dropwise at −78° C. After stirring at −78° C. for 60 minutes, the reaction mixture was admixed with water and then warmed to room temperature. Then the mixture was admixed with water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated. Purification by column chromatography gives 3-fluoro-2-vinylbenzaldehyde (160 mg).
Workup
- temperaturewarmed to room temperature
- extractionextracted with ethyl acetate
- dry with materialThe combined organic phases were dried over sodium sulphate
- concentrationconcentrated
- customPurification by column chromatography
Sources & evidence
- ORD record
- ord-aa981a075a1c468fbf38ea8b619ec2d0
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09167821B2
Reaction notes
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