1-Tetralone → 5-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

Participants

Reaction Conditions

Reaction Steps

(Cornelius, L. A. H.; Combs, D. W. Synthetic Communications 1994, 24(19), 2777-2788) Into a round bottom flask kept at 0° C., AlCl3 (19.6 g, 146.8 mmol) was added and the reaction system was put under nitrogen. 8 mL of tetralone (8.62 g, 58.9 mmol) were added during a 10-minute period, at which point, the reaction mixture was heated in an oil bath at 90° C. for about 45 minutes before adding 3.6 mL of Br2 (11.2 g, 70.1 mmol). The reaction mixture was stirred at 90° C. for an hour before 30 mL of ice-water and 20 mL of NaHCO3 were added. The product was extracted twice from the aqueous phase with Et2O and, the resultant organic phase was washed once with NaHCO3, once with brine and dried under Na2SO4. The crude reaction mixture was purified by flash chromatography (2.5% EtOAc/97.5% hex) which afforded 5.87 g (26.1 mmol) of the product in a 44% yield.

Provenance & Evidence