Thionyl Chloride → 1-(Octahydro-isoindol-2-yl)-4-bromo-2-phenyl-butan-1-one

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Reaction Steps

4-Bromo-2-phenylbutanoic acid (4.86 g, 0.02 mol) and thionyl chloride (2.2 mL, 0.03 mol) were refluxed in dichloromethane (100 mL) under nitrogen for 3 hours. The solution was evaporated and flushed with benzene three times. The residue was dissolved in diethyl ether (50 mL) and cooled in an ice bath. Octahydroisoindole (2.5 g, 0.02 mol) and diisopropylethylamine (3.5 mL, 0.02 mol) dissolved in diethyl ether (50 mL) were added and the reaction was stirred for 60 hours at room temperature. TLC (Uniplate/EtOAc) showed essentially complete reaction. The solution was washed with water, sat. NaHCO3, and dried (Na2SO4). Evaporation of solvent left crude product.

Provenance & Evidence