Triethylamine → 1-(3,4-Difluorobenzoyl)azetidine

Participants

Reaction Steps

3,4-Difluorobenzoic acid (1.03 g, 6.51 mmol) in CH2Cl2 (10 ml) was added SOCl2 (600 uL, 8.26 mmol) and DMF (3 drop). The reaction mixture was heated to reflux for 3 hr. The mixture was evaporated under vacuum and dried. The oil/solid mixture was taken into CH2Cl2 (20 mL) and added azetidine hydrochloride (731 mg, 7.82 mmol) and triethylamine (2.75 mL, 19.7 mmol). The reaction mixture was stirred at room temperature for 2 hr, quenched with 1 N HCl (60 mL) and extracted with EtOAc. The organic layers were dried over MgSO4 and concentrated to give pale yellow oil which was purified by flash column chromatography eluting with 30% EtOAc in hexanes to give a white solid (553 mg, 48% yield). 1H NMR (400 MHz, CDCl3) δ 7.50 (m, 1 H) 7.40 (m, 1 H) 7.16-7.25 (m, 1 H) 4.32 (d, J=6.82 Hz, 2 H) 4.24 (d, J=7.07 Hz, 2H) 2.33-2.42 (m, 2 H).

Provenance & Evidence