Boron Trichloride → 3-Hydroxy-2-methylbenzonitrile

Temperature

-78 °C

A solution of 3-methoxy-2-methylbenzonitrile [(1 g, 6.79 mmol) U.S. Pat. No. 5,965,766, p 6] and tetra nbutyl ammonium iodide (4.12 g, 17 mmol) in dichloromethane (15 mL) was cooled to −78° C. and purged with nitrogen. Boron trichloride (1M in dichloromethane, 17 mL, 17 mmol) was added dropwise and the mixture was stirred for 15 minutes at −78° C. and at room temperature for 3 hours. The reaction mixture was quenched with water, stirred for 30 minutes and concentrated in vacuo. The aqueous residue was extracted with diethyl ether and the organic solution was washed with water (×5), dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a brown solid in 91% yield, 826 mg. 1H NMR (400 MHz, CDCl3) δ: 2.20 (s, 3H), 7.10 (m, 1H), 7.20 (d, 1H), 10.10 (s, 1H); LRMS APCI m/z 132 [M−H]−

1. custompurged with nitrogen
2. customThe reaction mixture was quenched with water
3. stirringstirred for 30 minutes
4. concentrationconcentrated in vacuo
5. extractionThe aqueous residue was extracted with diethyl ether
6. washthe organic solution was washed with water (×5)
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated in vacuo

ORD record

ord-6b85009b092842f393f3104c2fa1013f

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08207198B2