反应详情

温度

135 °C

In an open flask, thiophenol (2.86 g., 13 mmoles), cuprous oxide (1.86 g., 13 mmoles) and dimethyl formamide (30 ml.) were combined and heated in a 135° C. oil bath. The reaction mixture was allowed to cool slightly, 5-bromothiophene-3-carboxylic acid [2.5 g., 13 mmoles; Fournari et al., Bull. Chim. Soc. Fr., 4115 (1967)] in 50 ml. of dimethylformamide was added, and the mixture refluxed for 2 days. The reaction mixture was cooled, clarified by filtration, the filtrate evaporated to an oil, the oil triturated with 1 N hydrochloric acid, and gummy solids recovered by filtration and taken up in 1 N sodium hydroxide. The basic solution was extracted with ether, reacidified with conc. hydrochloric acid, product recovered by filtration, triturated with hexane and refiltered (912 mg., m.p. 97°-100° C., m/e 220). Recrystallization from methanol/water afforded purified 5-phenylthiofuran-3-carboxylic acid (439 mg., m.p. 101°-103° C.).

1. temperatureto cool slightly
2. temperaturethe mixture refluxed for 2 days
3. temperatureThe reaction mixture was cooled
4. filtrationclarified by filtration
5. customthe filtrate evaporated to an oil
6. customthe oil triturated with 1 N hydrochloric acid, and gummy solids
7. filtrationrecovered by filtration
8. extractionThe basic solution was extracted with ether
9. filtrationrecovered by filtration
10. customtriturated with hexane
11. customRecrystallization from methanol/water
12. customafforded
13. custompurified 5-phenylthiofuran-3-carboxylic acid (439 mg., m.p. 101°-103° C.)