反应详情

温度

60.5 °C

To a 4-L, jacketed glass reactor containing 2-(4-chlorophenyl)ethanol (Compound II) (501 g, 3199 mmol) and N,N-dimethylformamide (12.4 mL, 160 mmol) at 55° C. was slowly charged thionyl chloride (245 mL, 3359 mmol) over 120 min. The addition was exothermic with significant gas evolution. The reaction mixture was stirred for 2 h at 60 to 61° C. Reaction conversion was monitored by HPLC and 1H NMR. When the amount of 2-(4-chlorophenyliethanol remaining was <1 area % by HPLC, the reaction mixture was cooled to room temperature. The reaction mixture was placed under reduced pressure at 60° C. on a rotary evaporator to remove unreacted thionyl chloride. The reaction mixture (566 g) containing 1-chloro-4-(2-chloroethyl)benzene and N,N-dimethylformamide was isolated as a dark brown oil (99.52 area % by HPLC). 1H NMR (400 Hz, DMSO-d6) δ 3.05 (t, J=6.8 Hz, 2H), 3.87 (t, J=6.8 Hz, 2H), 7.33-7.41 (m, 4H).

1. customover 120 min
2. additionThe addition
3. customReaction conversion
4. temperaturethe reaction mixture was cooled to room temperature
5. customThe reaction mixture was placed under reduced pressure at 60° C. on a rotary evaporator
6. customto remove unreacted thionyl chloride
7. additionThe reaction mixture (566 g) containing 1-chloro-4-(2-chloroethyl)benzene
8. customN,N-dimethylformamide was isolated as a dark brown oil (99.52 area % by HPLC)