Réaction #1857588

Équation de réaction

water

1-bromo-3-fluoro-2-vinylbenzene

n-butyllithium

water

N,N-dimethylformamide

→

3-fluoro-2-vinylbenzaldehyde

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Températurewarmed to room temperature
2. 2
   Extractionextracted with ethyl acetate
3. 3
   SéchageThe combined organic phases were dried over sodium sulphate
4. 4
   Concentrationconcentrated
5. 5
   AutrePurification by column chromatography

Mode opératoire

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).

Source