Tin tetrachloride → Ethyl 6-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate

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Reaction Steps

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.

Provenance & Evidence