Hydrochloric Acid → 5-Cyano-2-fluorobenzaldehyde

Temperature

190 °C

To a solution of 5-bromo-2-fluorobenzaldehyde (1.93 g, 9.51 mmol) in DMF (4 mL) was added copper(I) cyanide (0.98 g, 10.93 mmol). The mixture was heated to 190 ° C. and stirred for 5 h. The dark brown reaction mixture was poured into a solution containing ferric chloride (3.0 g), conc. HCl (0.93 mL) and water (6 mL) and warmed to 65 ° C. for 20 min. The mixture was partitioned between toluene (20 mL) and water (20 mL). The organic was washed with diluted HCl (25 mL), water (20 mL), 10% sodium hydroxide (25 mL), dried over magnesium sulfate, and concentrated to provide a solid product:

1. additionThe dark brown reaction mixture was poured into a solution
2. temperaturewarmed to 65 ° C. for 20 min
3. customThe mixture was partitioned between toluene (20 mL) and water (20 mL)
4. washThe organic was washed with diluted HCl (25 mL), water (20 mL), 10% sodium hydroxide (25 mL)
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated
7. customto provide a solid product

ORD record

ord-23b8f102b85645a89afc361eb1179410

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06376499B1