Hydroxyamine hydrochloride → HCID 118005884, compound

Participants

Reaction Conditions

Reaction Steps

Hydroxylamine hydrochloride (0.5 g, 7.9 mmol) was added to a solution of 32 (1.0 g, 4.0 mmol) in DMSO (5.0 mL), and the mixture was stirred for 16 h at 100° C. After cooling to room temperature, the mixture was diluted with ethyl acetate (100 mL), and washed with saturated NaHCO3 aqueous solution (2×50 mL). The organic was dried over anhydrous Na2SO4, filtered, concentrated by rotary evaporation, and purified by column chromatography to give 5-bromo-7-fluoro-2-naphthonitrile (33) (28%). 1H NMR (400 MHz, CDCl3) δ 10.20 (s, 1H), 8.34 (d, J=8.8 Hz, 1H), 8.29 (s, 1H), 8.01 (d, J=8.8 Hz, 1H), 7.77 (dd, J=8.0, 2.3 Hz, 1H), 7.64 (d, J=8.6 Hz, 1H). GC-MS (ES) for C11H5BrFN [M+1]+ 250.

Provenance & Evidence