[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([F:11])[CH:5]=1)=[O:3].BrBr.ClC1C=C(Cl)C=CC=1C(=O)C[Br:19].C(C1C=CC=CC=1C(=O)CBr)C.C(C1C=CC(C(=O)CBr)=CC=1)(C)C.C(C1C=C(C=CC=1)C(=O)CBr)C(C)C.CC1C=C(C=CC=1C)C(=O)CBr.C(OC1C=C(C=CC=1)C(=O)CBr)C.C(OC1C=CC(C(=O)CBr)=CC=1)(C)C.C(OC1C=C(C=CC=1OCC)C(=O)CBr)C.FC1C=CC(F)=CC=1C(=O)CBr>C(Cl)(Cl)Cl.C(O)(=O)C>[F:11][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[F:10])[C:2](=[O:3])[CH2:1][Br:19]To a solution of 10.1 g. (0.065 mole) of 3,4-difluoroacetophenone in 100 ml. of glacial acetic acid was added 3.4 ml. (0.065 mole) of bromine dropwise. When the addition was complete the solution was stirred for 0.5 hr. and then stripped to dryness under reduced pressure. The residue was dissolved in chloroform and washed with aqueous sodium bicarbonate. Evaporation of the organic phase provided 14.8 g. (97%) of colorless liquid product. Similarly prepared were 2,4-dichlorophenacyl bromide, o-ethylphenacyl bromide, p-isopropylphenacyl bromide, m-isobutylphenacyl bromide, 3,4-dimethylphenacyl bromide, m-ethoxyphenacyl bromide, p-isopropoxyphenacyl bromide, 3,4-diethoxyphenacyl bromide, and 2,5-difluorophenacyl bromide.
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