Pyridine → 2-(2-Nitrophenyl)propyl chloride

Participants

Reaction Steps

12.16 g thionyl chloride (7.5 ml, 102 mmol) in 10 ml toluene (abs.) are added quickly in a drop-wise manner to 6.2 g 2-(2-nitrophenyl)propanol (34 mmol) in 90 ml abs. toluene and 2 ml pyridine. The reaction solution is heated 1 h under reflux. After cooling, this is poured onto 100 g ice and mixed with 80 ml CH2Cl2. The H2O phase is extracted 2× each with 80 ml CH2Cl2. The combined organic phases are neutralized with 120 ml saturated bicarbonate solution, dried over Na2SO4 and rotary evaporated. 6.62 g (33 mmol, 98%) 2-(2-nitrophenyl)propyl chloride are obtained as a brown oil.

Provenance & Evidence