Boron tribromide → 2-Amino-3-hydroxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-3-methoxybenzonitrile (Example 127b) (0.98 g, 6.59 mmol) in CH2Cl2 (25.0 mL), a solution of BBr3 in CH2Cl2 (1.0M, 19.8 mL, 19.77 mmol) was added drop wise at −78° C. under a nitrogen atmosphere. The obtained mixture was stirred at −78° C. for 30 min, and then at room temperature overnight. The reaction was quenched with water, basified with saturated aqueous NaHCO3 (pH˜8) and extracted with CH2Cl2. The combined extract was dried with MgSO4, filtered and evaporated. The title compound was obtained in amount of 0.80 g (91%) as orange solid and was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 9.86 (broad s, 1H), 6.82-6.87 (m, 2H), 6.46 (t, J=8.0 Hz, 1H), 5.34 (broad s, 2H).

Provenance & Evidence