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

Temperature

120 °C

A mixture of (3-bromo-phenyl)-acetic acid ethyl ester (9.15 g, 37.6 mmol), copper cyanide (5.06 g, 56.5 mmol), and 1-methyl-2-pyrrolidinone (80 mL) was placed into an oil bath heated at 120° C. behind a protective shield. The reaction was heated to 200° C. for 1 h and additional copper cyanide (spatula tip) was added. After heating for an additional 0.5 h, the reaction was cooled to room temperature. The reaction was diluted with EtOAc and the organic solution was washed with water/ammonium hydroxide solution (2:1 v/v) until the aqueous solution was no longer blue. The organic solution was washed with brine, dried (MgSO4), filtered, and concentrated. Flash chromatography (9:1 hexanes:EtOAc) provided (3-cyano-phenyl)-acetic acid ethyl ester (6.31 g) as a clear oil which solidified on standing. 1H NMR (400 MHz, CDCl3) δ 7.57-7.50 (m, 3H), 7.42 (m, 1H), 4.15 (q, 2H), 3.63 (s, 2H), 1.24 (t, 3H).

1. customwas placed into an oil bath
2. temperatureThe reaction was heated to 200° C. for 1 h
3. temperatureAfter heating for an additional 0.5 h
4. temperaturethe reaction was cooled to room temperature
5. washthe organic solution was washed with water/ammonium hydroxide solution (2:1 v/v) until the aqueous solution
6. washThe organic solution was washed with brine
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-f5ff05dd80dc4e70bfeeb6d7c58d6a33

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06288120B1