Boron Trichloride → 3-Hydroxy-5-methylbenzonitrile

Temperature

-78 °C

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).

1. temperaturewarmed up to room temperature overnight
2. customThe reaction mixture was quenched with ice and neutralized with saturated NaHCO3 solution
3. additionDCM was added
4. extractionto extract the reaction mixture
5. concentrationThe organic layer was concentrated down
6. custompurified (silica gel, 0-10% MeOH/DCM)

ORD record

ord-82dd51ece52c42f7aab2dd60cd6f9534

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08334295B2