Boron Trichloride → 3-Hydroxy-5-methylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

In a 100 mL round bottom flask, 3-methoxy-5-methyl-benzonitrile (500 mg, 3.39 mmol) was dissolved in 15 mL dry DCM, and tetrabutylammonium iodide (1.38 g, 3.73 mmol, 3.5 eq.) was added. The flask was cooled to −78° C. BCl3 (1 M in DCM, 11.87 mL, 33.16 mmol) was added to the reaction dropwise. The reaction mixture was stirred at −78° C. and warmed up to room temperature overnight. The reaction mixture was quenched with ice and neutralized with saturated NaHCO3 solution. DCM was added to extract the reaction mixture. The organic layer was concentrated down and purified (silica gel, 0-10% MeOH/DCM) to give a light yellow solid (408 g, 90%). LC-MS shows 132.0 (M−1). 1H NMR (300 MHz, CDCl3): δ 7.20 (s, 1H), 6.96 (s, 1H), 6.91 (s, 1H), 2.37 (s, 3H).

Provenance & Evidence