Hydrogen Bromide → Benzene, 1-bromo-3-ethyl-

Participants

Reaction Conditions

Reaction Steps

To an aqueous 50% sulfuric acid solution (43.6 g) containing 3-ethylaniline (10.0 g, 82.5 mmol) was added dropwise an aqueous solution (16.5 mL) of sodium nitrite (6.83 g, 99.0 mmol) at 0° C. over 30 min. The obtained reaction mixture was stirred at 0° C. for 45 min. A solution of this diazonium salt was added by small portions to a 48% hydrobromic acid solution (82.5 mL) containing copper(I) bromide (12.4 g, 86.6 mmol) with heating under gentle reflux. After the addition, the reaction mixture was heated under reflux for 30 min. The reaction mixture was cooled to room temperature and extracted with ethyl ether. The extract was washed successively with 1N aqueous sodium hydroxide solution and saturated brine, filtered, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=20:1) to give the title compound (6.13 g, yield 40%).

Provenance & Evidence