反应详情

温度

80 °C

Ethyl 4-fluorobenzoate (5.00 g, 29.7 mmol) and tert-butylsulfanylsodium (6.67 g, 59.5 mmol) were combined in DMF (50 mL). The reaction mixture was heated at 80° C. for 67 hours. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (100 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield ethyl 4-tert-butylsulfanylbenzoate. The aqueous layer was acidified with hydrochloric acid. The aqueous layer was extracted with ethyl acetate (3×100 mL), and the combined organic layer was washed with water (1×50 mL) and brine (1×50 mL). The organic layer was dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield 4-(tert-butylthio)benzoic acid as an off-white solid. 1H NMR (400 MHz, DMSO) δ 13.10 (s, 1H), 7.93 (d, J=8.2 Hz, 2H), 7.61 (d, J=8.2 Hz, 2H), 1.28 (s, 9H). ESI-MS m/z calc. 210.1, found 211.1 (M+1)+; Retention time: 1.64 minutes (3 min run).

1. customThe reaction mixture was partitioned between ethyl acetate (100 mL) and water (100 mL)
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
4. dry with materialThe combined organic layers were dried over sodium sulfate
5. filtrationfiltered
6. customthe solvent was evaporated under reduced pressure