反应详情

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.

1. temperatureThe reaction mixture was cooled
2. filtrationfiltered
3. additionthe filtrate diluted with 500 ml
4. customof water and insolubles removed by filtration
5. extractionwas extracted into ethyl acetate
6. customrecovered by evaporation to an oil
7. customcrystallized by trituration with water (860 mg.)
8. customTwo crystallizations from methanol/water
9. customgave
10. custompurified 5-(4-chlorophenylthio)furan-3-carboxylic acid (150 mg., m.p. 142°-145° C., m/e 254)