Potassium Iodide → HCID 117737273, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate (150 g, 479 mmol, 1.0 equiv) in acetonitrile (2.0 L) was added para-toluenesulfonic acid monohydrate (273.16 g, 1437 mmol, 3.0 equiv, Spectrochem). The reaction mixture was cooled to 0° C. and a solution of sodium nitrite (66.03 g, 958 mmol, 2.0 equiv, Spectrochem) and potassium iodide (185.7 g, 1198 mmol, 2.5 equiv, Spectrochem) in water (450 mL) was added drop wise keeping temperature below 5° C. The reaction mixture was stirred at 0° C. for 5 h. The mixture was then diluted with ethyl acetate (5.0 L) and quenched with 2M aqueous sodium hyposulfite solution (5.0 L). The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate solution (3.0 L). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude material which was purified by column chromatography (silica gel; mesh size 60-120, elution 0-5% ethyl acetate in hexane) to yield ethyl-3-(5-(benzylthio)-2-iodophenyl)acrylate (130 g, 64%) as light brown solid. TLC solvent system: 20% ethyl acetate in hexane. Product's Rf: 0.6. MS (ESI, positive ion) m/z; 425.0 (M+1)

Provenance & Evidence