Toluene → 3,5-Dimethylbenzonitrile

Temperature

110 °C

An oven dried 100 mL three necked round bottom flask was charged, under positive pressure of argon, with NaCN (2.04 g, 41.6 mmol) CuI (660 mg, 3.47 mmol, 10 mol %), KI (1.14 g, 6.87 mmol, 20 mol %), and anhydrous toluene (25 mL). N,N′-Dimethylethylenediamine (3.7 mL, 35 mmol) and 5-bromo-m-xylene (4.7 mL, 35 mmol) were added dropwise under mechanical stiring. The reaction mixture was stirred at 110° C. for 24 h. The resulting suspension was allowed to reach room temperature, diluted with 30% aq ammonia (20 mL) and extracted with toluene (2×10 mL). The combined organic phases were dried over MgSO4, concentrated, and the residue was purified by distillation under reduced pressure (bp 100° C. @10 Torr) to provide the desired product as a white crystalline solid (4.08 g, 90% yield). Mp 42-43° C. (lit. 42.9° C., See Birch, S. F.; Dean, R. A.; Fidler, F. A.; Lowry, R. A. J. Am. Chem. Soc. 1949, 71, 1362). 1H NMR (400 MHz, CDCl3; lit. See Nomura, Y.; Takeuchi, Y. Tetrahedron 1969, 25, 3825): δ 7.27 (s, 2H), 7.23 (s, 1H), 2.36 (s, 6H); 13C NMR (100 MHz, CDCl3): 139.4, 135.0, 130.1, 119.7, 112.4, 21.5; IR (neat, cm−1): 2230, 1605, 1378, 907, 854, 682. Anal. Calcd. for C9H9N: C, 82.41; H, 6.92; N, 10.68. Found: C, 82.11; H, 6.88, N, 10.52.

1. dry with materialAn oven dried 100 mL three necked round bottom flask
2. customto reach room temperature
3. extractionextracted with toluene (2×10 mL)
4. dry with materialThe combined organic phases were dried over MgSO4
5. concentrationconcentrated
6. distillationthe residue was purified by distillation under reduced pressure (bp 100° C. @10 Torr)

ORD record

ord-e6c22d9ef4a64ff29dd42ad1f5bf596e

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07323608B2