Acetyl chloride → 1-(6-Bromonaphthalen-2-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromonaphthalene (41.4 g, 200 mmol), acetyl chloride (11.3 mL, 160 mmol), nitrobenzene (250 mL) and AlCl3 (28 g, 210 mmol) was stirred for 4 hours at 100° C. (oil bath temperature). The resulting reaction mixture was cooled, poured onto ice/water (100 mL) and filtered. The filtrate was washed with water (100 mL). The solvent (nitrobenzene) was removed by distillation. The resulting residue was crystallized from hexane to afford 18 g of desired product (36% yield). 1-(6-bromonaphthalen-2-yl)ethanone: 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm 2.66 (s, 3H) 7.66 (dd, J=8.8, 2.0 Hz, 1H) 7.86 (d, J=8.8 Hz, 1H) 7.94 (d, J=8.8 Hz, 1H) 8.02 (dd, J=8.8, 1.8 Hz, 1H) 8.13 (d, J=2.0 Hz, 1H) 8.53 (d, J=1.8 Hz, 1H).

Provenance & Evidence