[OH-].[Na+].Br[CH:4]([Br:10])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Cl:11][C:12]1[CH:13]=[C:14]([CH:23]=[CH:24][C:25]=1[OH:26])[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Br:10][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:26][C:25]1[CH:24]=[CH:23][C:14]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])=[CH:13][C:12]=1[Cl:11]100 ml of a 10 percent aqueous sodium hydroxide solution are added to a solution of 34.5 g of dibromohexane, 9.9 g of 3-chloro-4-hydroxybenzophenone and 1.6 g of tetrabutylammonium bromide in 100 ml of methylene chloride. The heterogeneous mixture is stirred at room temperature overnight. The organic phase is separated, dried over sodium sulfate and evaporated. By chromatography of the residue on silica gel with hexane/ethyl acetate 7:3, there is obtained 4-[(6-bromohexyl)oxy]-3-chlorobenzophenone, m.p. 58° C.
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