Hydrochloric Acid → 4-Bromo-2,6-dimethylbenzonitrile

Temperature

0 °C

A mixture of 4-bromo-2,6-dimethylbenzenamine (20 g, 100 mmol) and conc. HCl (100 mL) in water (100 mL) was sonicated for 5 min and then cooled to 0° C. A solution of sodium nitrite (6.9 g, 100 mmol) in water (25 mL) was added, and the resulting mixture was stirred at 0° C. for 30 min, then neutralized by the addition of solid sodium bicarbonate. The resulting mixture was slowly poured (in portions) into a solution of potassium cyanide (6.5 g, 100 mmol) and copper(I) cyanide (9.0 g, 100 mmol) in water (50 mL). The resulting mixture was heated at 70° C. for 30 min, then cooled to 25° C. and extracted with EtOAc (3×150 mL). The combined extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to provide 4-bromo-2,6-dimethylbenzonitrile as a brown solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.56 (s, 2 H), 2.45 (s, 6 H).

1. customwas sonicated for 5 min
2. temperatureThe resulting mixture was heated at 70° C. for 30 min
3. temperaturecooled to 25° C.
4. extractionextracted with EtOAc (3×150 mL)
5. washThe combined extracts were washed with brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-c0e8057404014731925ed156802dee3a

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842685B2