Methanol → 7-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

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Reaction Steps

7-Bromo-1-tetralone thiosemicarbazone (21) Into a round bottom flask containing the appropriate ketone (0.347 g, 1.54 mmol), 10 mL of anhydrous methanol were added and the solution was refluxed for about 10 minutes. To the warm ketone solution, thiosemicarbazide (0.246 g, 2.70 mmol) and 0.7 mL of 1% solution of HOAc were added. The reaction mixture was refluxed under nitrogen atmosphere for 18 h, at which point, the solvent was evaporated. The crude reaction mixture was purified by flash chromatography (30% EtOAc/70% hex) which afforded 0.314 g (1.05 mmol) of the product in a 68% yield.

Provenance & Evidence