N-methyl-2-pyrrolidone → 4-(Benzyloxy)-2-fluorobenzonitrile

Compound 20 (10.00 g, 35.7 mmol) and cuprous cyanide (13.00 , 71.4 mmol) were suspended in 1-methyl-2-pyrollidinone (250 ml) and heated under reflux for 24 h. The reaction mixture was cooled to room temperature and filtered through ‘hyflo’ to remove the excess cuprous cyanide. Water (200 ml) was added to the solution which was subsequently washed with ether (2×400 ml). The combined ether extracts were then washed with water (2×500 ml) and brine (500 ml) and then dried (MgSO4). The drying agent was filtered off and the solvent removed in vacuo to yield an off-white solid which was purified by column chromatography (dichloromethane) on silica to yield colourless crystals. Yield 5.79 g (71%).

1. temperatureheated
2. temperatureunder reflux for 24 h
3. filtrationfiltered through ‘hyflo’
4. customto remove the excess cuprous cyanide
5. additionWater (200 ml) was added to the solution which
6. washwas subsequently washed with ether (2×400 ml)
7. washThe combined ether extracts were then washed with water (2×500 ml) and brine (500 ml)
8. dry with materialdried (MgSO4)
9. filtrationThe drying agent was filtered off
10. customthe solvent removed in vacuo
11. customto yield an off-white solid which
12. customwas purified by column chromatography (dichloromethane) on silica
13. customto yield colourless crystals

ORD record

ord-da16493528ee4dbe872a115cfbfbdd48

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06666989B1