2-Chloroanisole → 3-Chloro-4-methoxybenzene-1-sulfonyl chloride

Participants

Reaction Steps

A stirred solution of 2-chloroanisole (8.90 mL, 70.1 mmol) in chloroform (100 mL) was cooled to 0° C., and treated drop-wise with chlorosulfonic acid (9.3 mL, 140 mmol). After stirring at room temperature for 14 hours, the reaction mixture was poured into ice-water (250 mL) and the separated, aqueous phase extracted with chloroform (2×50 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to a viscous oil which crystallized upon standing (8.58 g, 52%), m.p. 78° C.;

Provenance & Evidence