[C:1]1(C)C=CC=CC=1.C[Zn]C.[F:11][C:12]([F:24])([F:23])[C:13]1[CH:22]=[CH:21][C:16]([C:17](Cl)([CH3:19])[CH3:18])=[CH:15][CH:14]=1>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[F:11][C:12]([F:24])([F:23])[C:13]1[CH:22]=[CH:21][C:16]([C:17]([CH3:1])([CH3:19])[CH3:18])=[CH:15][CH:14]=1To a toluene solution of dimethylzinc (150 mL, 2.0M, 0.30 mol) at -78° C. is added a CH2Cl2 solution of titanium tetrachloride (150 mL, 1.0 M, 0.15 mol) and after stirring for 30 min 4-trifluoromethyl-α,α-dimethylbenzyl chloride (83.3 g, 0.373 mol) in CH2Cl2 (100 mL) is added dropwise over 20 min. After the addition is complete the reaction is allowed to warm to -40° C. over 1.5 h. After an additional 2 h at -40° C. the brown reaction mixture is carefully poured onto crushed ice, extracted with CH2 Cl2 (2×500 mL), the combined extracts dried over MgSO4 and concentrated to give 4-trifluoromethyl-t-butylbenzene; yield: 60.3 g (80%). Anal. Calcd. for C11H13F3 : C, 65.32; H, 6.48. Found: C, 65.11; H, 6.38.
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