2,5-Dimethyl-4-methoxyphenylacetonitrile → HCID 58907430, compound

Temperature

-80 °C

A solution of (4-methoxy-2,5-dimethylphenyl)acetonitrile (0.5 g, 2.9 mmol) in dichloromethane (10 mL) was cooled to −80° C. and treated with borontribromide (1M in dichloromethane, 14.3 mL, 14.3 mmol). The reaction mixture was stirred at −80° C. for a further 30 minutes and then was allowed to warm to room temperature over a period of 2 hours. The reaction mixture was quenched with saturated sodium hydrogen carbonate solution (20 mL) and the organic layer was separated. The organic solution was washed with brine (20 mL), dried over sodium sulfate and the concentrated in vacuo to afford a pale brown solid. Purification by column chromatography on silica gel, eluting with ethyl acetate:pentane 20:80 to 33:67, afforded the title compound as a colourless solid in 60% dispersion in mineral oil yield, 0.28 g. 1H NMR (400 MHz, CD3OD) δ: 2.13 (3H, s), 2.23 (3H, s), 3.66 (2H, s), 6.60 (1H, s), 6.98 (1H, s); LRMS ESI m/z 160 [M−H]−

1. temperatureto warm to room temperature over a period of 2 hours
2. customThe reaction mixture was quenched with saturated sodium hydrogen carbonate solution (20 mL)
3. customthe organic layer was separated
4. washThe organic solution was washed with brine (20 mL)
5. dry with materialdried over sodium sulfate
6. concentrationthe concentrated in vacuo
7. customto afford a pale brown solid
8. customPurification by column chromatography on silica gel
9. washeluting with ethyl acetate:pentane 20:80 to 33:67

ORD record

ord-15720642045a4c589cd31a5d1bb3bf7d

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547731B2