Bromobenzene → 1-Phenylazetidin-3-ol

Participants

Reaction Steps

A suspension of azetidin-3-ylbenzoate hydrochloride (600 mg), bromobenzene (530 mg), Pd2(dba)3 (129 mg), Xantphos (134 mg) and sodium tert-butoxide (515 mg) in toluene (12 mL) was irradiated with microwave at 150° C. for 30 min under an argon atmosphere. The reaction mixture was filtered and concentrated under reduced pressure. The residue was dissolved in ethanol (12 mL), and 1N aqueous sodium hydroxide solution (3 mL) was added. The reaction mixture was stirred at room temperature for 1 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate) to give the title compound (131 mg).

Provenance & Evidence