N-methyl-2-pyrrolidone → Ethyl 2-(3-cyanophenyl)acetate

Temperature

190 °C

To a mixture of of (3-bromo-phenyl)-acetic acid ethyl ester (15.3 g, 62.9 mmol) and 1-methyl-2-pyrrolidinone (125 mL) was added copper (I) cyanide (8.46 g, 94.4 mmol). The reaction mixture was stirred in an oil bath at 190° C. for 1 h. The reaction was cooled to room temperature and was diluted with EtOAc and 2:1H2O/NH4OH. The mixture was stirred for 10 minutes and was filtered through Celite. The aqueous layer was washed with EtOAc (2×). The organic solution was washed with 2:1 H2O/NH4OH until the aqueous extracts were no longer blue. The organic solution was dried over MgSO4, filtered and concentrated to afford (3-cyano-phenyl)-acetic acid ethyl ester (11.95 g). 1H NMR (400 MHz, CDCl3) δ 7.51-7.58 (m, 3H), 7.43 (t, 1H), 4.16 (q, 2H), 3.63 (s, 2H), 1.25 (t, 3H).

1. temperatureThe reaction was cooled to room temperature
2. stirringThe mixture was stirred for 10 minutes
3. filtrationwas filtered through Celite
4. washThe aqueous layer was washed with EtOAc (2×)
5. washThe organic solution was washed with 2:1 H2O/NH4OH until the aqueous extracts
6. dry with materialThe organic solution was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-b54fe9cc914d4492be99b246659579b3

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06288120B1