[Br:1]Br.[F:3][C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[C:6]=2[CH:5]=1.O>CCOCC>[F:3][C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][CH:11]([Br:1])[C:12](=[O:13])[C:6]=2[CH:5]=168.9 g of bromine are added dropwise to a solution of 73.1 g of 3-fluoro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one in 700 ml of ether under ice-cooling during 1 hour. After the mixture is stirred for 1 hour, the reaction mixture is poured into water and the mixture is extracted with ether. The ether layer is washed, dried and evaporated to remove the solvent to obtain 106.8 g of 3-fluoro-6-bromo-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one as an oil.
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