反应详情

Stannic chloride (0.41 g.) was added to a stirred solution of 5-nitrobenzo[b]thiophene (0.28 g.) and methyl 4-bromomethyl-3-methoxybenzoate (B) (0.61 g.) in dichloromethane (5 ml.). The mixture was heated under reflux for 18 hours. The cooled mixture was poured into water (10 ml.) and extracted with dichloromethane (2×20 ml.). The combined extracts were dried (MgSO4) and evaporated. The oil was purified by flash chromatography on silica gel (100 ml.) eluting with 1:9 v/v ethyl acetate:hexane. The solid obtained was crystallized from hexane to give methyl 3-methoxy-4-(5-nitrobenzo[b]thien-3-ylmethyl)benzoate (I) as a solid (0.16 g., 30%): NMR: (250 MHz, CDCl3) 3.92(s, 3H, OCH3), 3.98(s,3H, OCH3), 4.28(s,2H, CH2 --Ar), 7.15 (d,1H), 7.22(s,1H), 7.56(m,2H), 7.93(d,1H), 8.19(dd, 1H); 8.73(d,1H).

1. temperatureThe mixture was heated
2. temperatureunder reflux for 18 hours
3. extractionextracted with dichloromethane (2×20 ml.)
4. dry with materialThe combined extracts were dried (MgSO4)
5. customevaporated
6. customThe oil was purified by flash chromatography on silica gel (100 ml.)
7. washeluting with 1:9 v/v ethyl acetate
8. customThe solid obtained
9. customwas crystallized from hexane