反应详情

Tin(IV)chloride (6.67 mL of a 1 M solution in dichloromethane, 6.67 mmol) was added to N-[2-(3-bromophenyl)ethyl]benzenesulfonamide (1.08 g, 3.17 mmol) and ethyl chloro(methylthio)acetate (1.07 g, 6.35 mmol) in 1,2-dichloroethane (11 mL) under argon and the reaction was heated at reflux for 3 hours. After cooling, the mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:4 ethyl acetate:hexanes to give 1.07 g (79%) of ethyl 6-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate and 255.6 mg (19%) of ethyl 8-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate as oils.

1. temperaturethe reaction was heated
2. temperatureat reflux for 3 hours
3. temperatureAfter cooling
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with saturated sodium bicarbonate and brine
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by silica gel chromatography
10. washeluting with 1:4 ethyl acetate