Hydrogen Bromide → 7-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one

Participants

Reaction Conditions

Reaction Steps

To a cooled (10° C.) stirred solution of sodium nitrate (2.18 g, 13.92 mmol) in concentrated sulfuric acid (28.4 mL) and glacial acetic acid (26.27 mL) [prepared by adding sodium nitrate to cooled (10° C.) concentrated sulfuric acid, heating to dissolve, recooling and then adding glacial acetic acid] was added a solution of 4,4-dimethyl-7-amino-1-tetralone (XII) (5.0 g, 26.46 mmol) in glacial acetic acid (89 mL) over 10 minutes. The resulting solution was added slowly (over 10 minutes) to a heated (60° C.) solution of copper (I) bromide (16.66 g) in concentrated hydrobromic acid (159 mL). The mixture was warmed to 90° C. for 10 minutes, cooled, diluted with water (250 mL) and extracted with ethyl acetate (2×200 mL). The combined organic phases were concentrated in vacuo and the residue chromatographed on silica gel (eluted with 3% ethyl acetate in hexane) to give 1.95 g (Y: 29%) of the title compound; 1H-NMR (CDCl3): δ 8.13 (d,J=2.3 Hz, 1H), 7.62 (dd, J=8.5, 2.3 Hz, 1H), 7.31 (d, J=8.5 Hz, 1H), 2.73 (t, J=7.0 Hz, 2H), 2.01 (t, J=7.0 HZ, 2H), 1.38 (s, 6H); MS (DCI) m/e: 253 (MH+).

Provenance & Evidence