3,5-Difluorobenzonitrile → 3-Fluoro-5-methoxybenzonitrile

In a 250 ml round bottom flask equipped with stir bar added 3,5-Difluorobenzonitrile (4.2 g, 30.4 mmol), sodium methoxide (10.4 ml, 45.6 mmol, 25% methanol) and dimethylformamide (40 ml). Stirred the resulting reaction mixture at room temperature, overnight. The reaction mixture was concentrated in-vacuo and residue was dissolved in dichloromethane (200 ml). The organic phase was washed sequentially with water (150 ml) and brine (150 ml), dried. (sodium sulfate) and concentrated in-vacuo. The crude residue was purified on silica gel using 10% diethyl ether in hexanes to isolate 3-Fluoro-5-methoxybenzonitrile (1.63 g) as a white solid.

1. customIn a 250 ml round bottom flask equipped
2. stirringStirred
3. customthe resulting reaction mixture at room temperature
4. customovernight
5. concentrationThe reaction mixture was concentrated in-vacuo and residue
6. dissolutionwas dissolved in dichloromethane (200 ml)
7. washThe organic phase was washed sequentially with water (150 ml) and brine (150 ml)
8. customdried
9. concentration(sodium sulfate) and concentrated in-vacuo
10. customThe crude residue was purified on silica gel using 10% diethyl ether in hexanes

ORD record

ord-cb0d2676793545b0a94b1acac51c4e85

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07112595B2