Acetyl chloride → 1-(4-Tert-butyl-2-bromophenyl)ethanone

Participants

Reaction Steps

Aluminum chloride (8.0 g, 60 mmol) was stirred in CH2Cl2 (200 mL), and acetyl chloride (8.5 mL, 120 mmol) was slowly added, producing a homogeneous solution. A solution of 3-bromo tert-butyl benzene (11 g, 50 mmol) in CH2Cl2 (20 mL) was slowly added, and the reaction was stirred at room temperature 16 h. After being diluted with CH2Cl2, the reaction was washed with water, saturated aqueous NaHCO3, and water. The organic solution was dried over Na2SO4 and concentrated under vacuum. Purification by silica gel chromatography (0%-50% CH2Cl2-hexanes) afforded 1-(4-tert-butyl-2-bromophenyl)ethanone (3.1 g, 24% yield) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.61 (d, J=1.8 Hz, 1H), 7.46 (d, J=8.1 Hz, 1H), 7.37 (dd, J=8.1, 1.8 Hz, 1H), 2.63 (s, 3H), 1.32 (s, 9H) ppm.

Provenance & Evidence