[F:1][C:2]([F:15])([C:11]([F:14])([F:13])[F:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:28]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:28][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][C:2]([F:15])([F:1])[C:11]([F:13])([F:12])[F:14])=[CH:9][CH:8]=1To a solution of 4-(2,2,3,3,3-pentafluoropropyl)toluene (9.97 g, 39.4 mmol) in carbon tetrachloride (300 ml) were added 2,2′-azobisisobutyronitrile (0.33 g, 197 mmol) and N-bromosuccinimide (8.50 g, 47.3 mmol) and the mixture was heated under reflux overnight. After cooling to room temperature, insoluble material was filtered off, and the filtrated was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0, 50:1, 20:1) to give 1-(bromomethyl)-4-(2,2,3,3,3-pentafluoropropyl)benzene (3.66 g, 31% (yield by two steps)) as colorless crystals.
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