Pyridine → 2-(4-Chloro-2-nitrophenyl)ethyl chloride

Participants

Reaction Steps

12 g thionyl chloride (7.4 ml, 100 mmol) in 10 ml toluene (abs.) are quickly added in a drop-wise manner to a solution of 6.78 g 2-(4-chloro-2-nitrophenyl)ethanol (33 mmol) in 100 ml abs. toluene and 2.5 ml pyridine. This is heated 2 h under reflux, cooled, poured onto 100 g ice and mixed with 100 ml CH2Cl2. The aqueous phase is extracted 2× each with 50 ml CH2Cl2. The combined organic phases are neutralized 2× each with 80 ml saturated bicarbonate solution, dried over Na2SO4, filtered and rotary evaporated. 7.12 g (32 mmol, 98%) 2-(4-chloro-2-nitrophenyl)ethyl chloride are obtained as a brown oil which hardens to a brown solid after some days in the refrigerator.

Provenance & Evidence