Hydrochloric Acid → 4-Bromo-3-methoxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-3-methoxyaniline (4 g, 19.8 mmol) in water (22 mL) was added concentrated HCl (7 mL). After cooling to 0° C., a solution of sodium nitrite (1.5 g, 22 mmol) in water (5 mL) was added dropwise. The resulting mixture was stirred at 0° C. for 30 min. After neutralizing with solid potassium carbonate, the reaction mixture was added to a mixture of copper (I) cyanide (2.13 g, 23.8 mmol) and potassium cyanide (3.2 g, 50 mmol) in water (22 mL) at 70° C. The reaction mixture was stirred at 70° C. for 1 h. After cooling to room temperature, the reaction was extracted with toluene (100 mL*4). The combined extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 4-bromo-3-methoxybenzonitrile (1.7 g) as a yellow solid. 1HNMR (400 MHz, CDCl3) δ 7.64 (d, J=8.4 Hz, 1H), 7.14 (dd, J=8.0, 1.6 Hz, 1H), 7.09-7.10 (m, 1H), 3.87 (s, 3H).

Provenance & Evidence