Boron Trichloride → 3-Hydroxy-2-methylbenzonitrile

Temperatur

-78 °C

A solution of 3-methoxy-2-methylbenzonitrile [(1 g, 6.79 mmol) U.S. Pat. No. 5,965,766, p6] 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-Eintrag

ord-a91de27ee48c4ea5a47bb4f07022a2fd

Quelldatensatz

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09023872B2