Hydrogen Bromide → 6-Bromo-1-tetralone

Participants

Reaction Steps

6-aminotetralone (2.0 g, 12 mmol) was dissolved in 25% HBr (4.0 mL) at 0° C. and then, a solution of NaNO2 (1.0 g, 15 mmol) in water (4.0 mL) was added slowly. Afterwards, a solution of CuBr (1.8 g, 4.0 mmol) in 48% HBr (4.0 mL) was added and the reaction was stirred at room temperature for 1.5 h. The solution was quenched by adding water and extracted with EtOAc (3×10 mL). The combined organic layer was dried over anhydrous Na2SO4, concentrated by rotary evaporation, and purified by column chromatography to give 6-bromo-3,4-dihydronaphthalen-1(2H)-one (19) (66%). NMR was according to reference 5.

Provenance & Evidence