Formic Acid → 4-Amino-3-bromo-2,5-difluorobenzaldehyde
Reaction equation
[NH2:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#N)=[C:4]([F:11])[C:3]=1[Br:12].C(O)=[O:14]>[Ni]>[NH2:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=[O:14])=[C:4]([F:11])[C:3]=1[Br:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 4-amino-3-bromo-2,5-difluoro-benzonitrile (7 g, 30 mmol) in 95-97% formic acid (40 mL) was added Raney nickel (7 g, previously washed with water and methanol). The reaction mixture was heated to 75-85° C. for 2 h. The reaction was then cooled to room temperature and filtered through Celite, washing with dichloromethane and water. The dichloromethane layer was washed with aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered, and concentrated to afford 5 g (71%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 10.15 (s, 1H), 7.41-7.49 (m, 1H), 4.9 (br. s, 2H).