Hydrochloric Acid → Sodium 4-fluorobenzene sulfinate

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-fluorobenzenesulfonyl chloride (50.0 grams 257 mmol), sodium sulfite (48.6 grams, 386 mmol), and sodium bicarbonate (108 grams, 1.28 mol) in water was heated to 100° C. The resulting solution was stirred for 1.5 hours at 100° C. then cooled to room temperature, acidified by careful addition of concentrated hydrochloric acid and extracted with ethyl acetate (3 times 250 ml). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound of Step A as a solid (35.8 g). 1H NMR (400 MHz, CDCl3) δ9.78 (s, 1H), 7.77-7.67 (m, 2H), 7.21-7.15 (m, 2H). MS (APCI−) Calc.: 160.0, Found: 195.1 (M+35, Cl− adduct).

Provenance & Evidence