反应详情

A solution of 1.50 g (8.92 mmol) 3-(methylthio)benzoic acid (Aldrich) in 20 mL of dry dichloromethane is cooled to 0° C. and 1.86 mL (19.6 mmol) borane-methylsulfide complex (Aldrich) is added. The solution is allowed to reach room temperature and stirred overnight, then hydrochloric acid (4 M, 50 mL) is added and the resulting mixture is stirred for additional 2 h. The reaction mixture is extracted with ethyl acetate (50 mL, 3 times) and the collected organic phases are washed with 10% NaHCO3 solution and brine and volatiles evaporated under vacuum to yield 3-methylsulfanyl-phenyl)-methanol (1.20 g, content ca. 75%), which is directly used in the next step. Step B: A solution of 3-methylsulfanyl-phenyl)-methanol (1.20 g, content ca 75%) in dichloromethane (25 mL) and phosphorus tribromide (1 M in dichloromethane, 6.42 mL) is stirred for 3 h at room temperature. The reaction mixture is washed with NaHCO3 solution (10%, 10 mL, 2 times) and the remaining organic phase is dried (MgSO4) and volatiles are evaporated under reduced pressure to yield the title compound (1.35 g).

1. addition1.86 mL (19.6 mmol) borane-methylsulfide complex (Aldrich) is added
2. customto reach room temperature
3. stirringthe resulting mixture is stirred for additional 2 h
4. extractionThe reaction mixture is extracted with ethyl acetate (50 mL, 3 times)
5. washthe collected organic phases are washed with 10% NaHCO3 solution and brine and volatiles
6. customevaporated under vacuum
7. customto yield 3-methylsulfanyl-phenyl)-methanol (1.20 g, content ca. 75%), which
8. washThe reaction mixture is washed with NaHCO3 solution (10%, 10 mL, 2 times)
9. dry with materialthe remaining organic phase is dried (MgSO4) and volatiles
10. customare evaporated under reduced pressure