thionyl chloride in benzene 1 h; Heating;

1: 1.a) diisopropylamine, n-BuLi; 2.a) HMPA / 1.a) THF, hexane, 0 deg C, 10 min; 1.b) THF, hexane, 0 deg C, 30 min; 2.a) THF, hexane, -50 deg C, 1 h; 2.b) r.t., overnight 2: 95.8 g / trifluoroacetic acid / CH2Cl2 / 5 h / Ambient temperature 3: 77.8 g / thionyl chloride / benzene / 1 h / Heating View Scheme

1: 1.a) diisopropylamine, n-BuLi; 2.a) HMPA / 1.a) THF, hexane, 0 deg C, 10 min; 1.b) THF, hexane, 0 deg C, 30 min; 2.a) THF, hexane, -50 deg C, 1 h; 2.b) r.t., overnight 2: 95.8 g / trifluoroacetic acid / CH2Cl2 / 5 h / Ambient temperature 3: 77.8 g / thionyl chloride / benzene / 1 h / Heating View Scheme

1: 95.8 g / trifluoroacetic acid / CH2Cl2 / 5 h / Ambient temperature 2: 77.8 g / thionyl chloride / benzene / 1 h / Heating View Scheme