Thionyl Chloride → 4-Chloro-6-(chloromethyl)-1,3-dioxaindane

Participants

Reaction Steps

A mixture of (7-chloro-1,3-benzodioxol-5-yl)methanol (34.5 g, 0.185 mol) and SOCl2 (5.0 mL, 67 mmol) in dichloromethane (200 mL) was stirred at room temperature for 1 h and was then poured into ice water. The organic layer was separated and the aqueous phase was extracted with dichloromethane (3×150 mL). The combined extracts were washed with water and aqueous NaHCO3 solution, dried over Na2SO4 and evaporated under reduced pressure to afford the title compound (30.0 g; 80%), which was directly used in the next step.

Provenance & Evidence