p-Chlorothiophenol → 5-(4-Chlorophenylthio)furan-3-carboxylic Acid

Participants

Reaction Steps

p-Chlorothiophenol (4.52 g., 31.4 mmoles) was reacted with 5-bromo-furan-3-carboxylic acid according to the procedure of Example 15, except that the total volume of dimethylformamide was 85 ml., and the reflux period was 8 hours. The reaction mixture was cooled, filtered, the filtrate diluted with 500 ml. of water and insolubles removed by filtration. The latter filtrate was made acidic with 6 N hydrochloric acid, product was extracted into ethyl acetate and recovered by evaporation to an oil, crystallized by trituration with water (860 mg.). Two crystallizations from methanol/water gave purified 5-(4-chlorophenylthio)furan-3-carboxylic acid (150 mg., m.p. 142°-145° C., m/e 254). Analysis: Calcd. for C11H7O3SCl; C, 51.87; H, 2.77. Found: C, 51.97; H, 2.99.

Provenance & Evidence