1-Chloro-1-(4-methoxyphenyl)-1-trifluoromethylethane → 1-Methoxy-4-(1,1,1-trifluoro-2-methylpropan-2-yl)benzene

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of TiCl4 (57 mg, 0.30 mmol) in dry CH2Cl2 (5 ml) was added a solution (1.05 mol/l) of ZnMe2 (0.87 ml, 0.91 mmol) in toluene via a syringe at −78° C. After 15 min, to this was added a solution of Compound 69 (217 mg, 0.91 mmol) in dry CH2Cl2 (2 ml) at same temperature. The reaction mixture was stirred at −78° C. for 1 h and warmed to room temperature. After 2 h, the mixture was diluted with water and stirred for 10 min. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was washed with brine, dried(MgSO4) and concentrated in vacuo to give crude product (200 mg) (Compounds 69:70=1:2.4) as a pale yellow oil. This was employed in the next step without further purification.

Provenance & Evidence