Ammonium Chloride → HCID 65920453, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-1,2-difluorobenzene (2.3 g, 11.8 mmol) in dry diethylether (20 ml) at −78° C., under nitrogen was added n-butyllithium (2.5 M in hexane, 4.7 ml, 11.8 mmol) dropwise. The mixture was stirred for 1 h after which a solution of 1-Boc-3-azetidinone (2.0 g, 11.7 mmol) in dry diethyl ether (20 mL) was added dropwise. The resulting mixture was stirred at −78° C. for 15 min and then brought to ambient temperature and stirred for 2 h. Aqueous ammonium chloride (50 mL, 50%) and diethylether was added, the organic phase was collected and the aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane 1:4 to 1:1) to give the title compound (1.9 g). MS m/z (rel. intensity, 70 eV) 285 (M+, 1), 156 (55), 141 (69), 127 (bp), 57 (88).

Provenance & Evidence