Methanol → 2-Chloro-5-nitrophenol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-chloro-2-methoxy-4-nitrobenzene (20 g, 106.6 mmol) in dichloromethane (500 mL) at −78° C. under a flow of Nitrogen gas, a solution of BBr3 (747 mmol) in dichloromethane was added dropwise. The reaction was stirred overnight at −20° C., then for 1 h at 4° C. To the reaction, 10 mL of MeOH and 100 mL of water were added dropwise. The resulting mixture was made basic with 10% NaOH solution. The aqueous layer was then made acidic and was extracted with chloroform. The combined organic layers were dried with Na2SO4, filtered and concentrated in vacuo to afford the yellow solid 2-chloro-5-nitrophenol (12.5 g, 68%).

Provenance & Evidence