Dimethylformamide → Methyl 3-(cyanomethyl)benzoate

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 LiCl followed 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. temperaturewas heated at 40–45° C. for 45 minutes
2. temperatureThe reaction was heated at 40° C. for 24 h
3. temperaturewas cooled to room temperature
4. temperatureThe reaction was heated at 40° C. for 18 h
5. temperaturewas cooled to room temperature
6. extractionthe product was extracted into EtOAc (3×25 mL)
7. washThe combined organic layers were washed with 1N LiCl
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-ac765f9655654a7f94e191e1f8737cd2

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06998423B2