Dimethylformamide → Methyl 3-(cyanomethyl)benzoate

Temperature

42.5 °C

A mixture of 3-bromomethyl-benzoic acid methyl ester (3.00 g, 13.10 mmol), potassium cyanide (1.02 g, 15.71 mmol) and DMF (25 mL) was heated at 40-45° C. for 45 minutes and was stirred at room temperature for 18 h. The reaction was heated at 40° C. for 24 h, was cooled to room temperature, and additional potassium cyanide (1.02 g, 15.71 mmol) was added. The reaction was heated at 40° C. for 18 h and was cooled to room temperature. Water (25 mL) was added and the product was extracted into EtOAc (3×25 mL). The combined organic layers were washed with 1N LiC1followed by brine, dried over MgSO4, filtered, and concentrated. Flash chromatography (9:1 hexanes:EtOAc to 4:1 hexanes:EtOAc) provided 3-cyanomethyl-benzoic acid methyl ester (1.36 g). MS 193 (M+18).

1. temperatureThe reaction was heated at 40° C. for 24 h
2. temperaturewas cooled to room temperature
3. temperatureThe reaction was heated at 40° C. for 18 h
4. temperaturewas cooled to room temperature
5. extractionthe product was extracted into EtOAc (3×25 mL)
6. washThe combined organic layers were washed with 1N
7. dry with materialby brine, dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-a714d8d3abda4800a3f3ba82c382ed0a

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06288120B1