(3-Bromopropyl)benzene → HCID 66911621, compound

Participants

Reaction Conditions

Reaction Steps

4-Chlorophenylhydrazine hydrochloride (550 mg, 3 mmol) was added to a vigorously stirred mixture of tetra-n-butylammonium chloride (42 mg, 0.15 mmol) in 50% aqueous sodium hydroxide (3 mL) followed by 1-bromo-3-phenylpropane (670 mg, 3.3 mmol). The reaction was heated to 60° C. (oil bath temperature) for 6 h. The reaction was cooled and diluted with water (30 mL) and extracted with chloroform (3×10 mL). The combined organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure to a dark red oil (690 mg). The oil was subjected to column chromatography (silica gel, eluent: 50% dichloromethane in hexane followed by 100% dichloromethane) to give a dark yellow oil (154 mg, 20%).

Provenance & Evidence