[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[FH:10].F.F.C(N(CC)CC)C.[Br:20]N1C(=O)CCC1=O>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([F:10])[CH2:7][Br:20])=[CH:4][CH:3]=15.0 g (27.31 mmol) of 4-bromostyrene were dissolved in 40 ml of dichloromethane and cooled to 0° C., and 13.21 g (81.94 mmol) of triethylamine trihydrofluoride were added. 5.83 g (32.78 mmol) of N-bromosuccinimide were then added in three portions. The mixture was stirred at RT overnight. After dilution with dichloromethane, the reaction mixture was poured onto ice-water. The organic phase was washed successively with 1 N hydrochloric acid, water and saturated sodium bicarbonate solution, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase pentane). This gave 4.14 g (53.8% of theory) of the title compound.
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