Thionyl Chloride → (E)-2-(3-Chloroprop-1-en-1-yl)-1,4-difluorobenzene

反応式

S(Cl)([Cl:3])=O.N1C2C=CC=CC=2N=N1.[F:14][C:15]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:16]=1[CH:17]=[CH:18][CH2:19]O>ClCCl>[Cl:3][CH2:19]/[CH:18]=[CH:17]/[C:16]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:15]=1[F:14]

参加物

実験手順

A solution of 0.34 cm3 (4.66 mmol) of thionyl chloride and 0.555 g (4.66 mmol) of benzotriazole in 40 cm3 of dichloromethane is added at a temperature in the region of 20° C. under an argon atmosphere to 0.646 g (3.8 mmol) of 2,5-difluorocinnamyl alcohol in solution in 40 cm3 of dichloromethane. After stirring for 10 minutes, the reaction mixture is filtered on No. 3 sintered glass and the solid residue rinsed with twice 10 cm3 of dichloromethane. The filtrate is washed 3 times with 30 cm3 of water. The organic phase is dried over magnesium sulfate and filtered to give a solution of 2-[(1E)-3-chloro-1-propenyl]-1,4-difluorobenzene (3.8 mmol) which is then concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 20° C., before dissolution in acetonitrile.