Sodium Hydroxide → 2-chloro-6-fluoro-4-(1H-pyrazol-3-yl)benzonitrile
Reaction equation
Cl.[Cl:2][C:3]1[CH:10]=[C:9]([C:11]2[NH:15][N:14]=[CH:13][CH:12]=2)[CH:8]=[C:7]([F:16])[C:4]=1[C:5]#[N:6].[OH-].[Na+]>C1COCC1>[Cl:2][C:3]1[CH:10]=[C:9]([C:11]2[NH:15][N:14]=[CH:13][CH:12]=2)[CH:8]=[C:7]([F:16])[C:4]=1[C:5]#[N:6]Participants
4
Procedure
2-Chloro-6-fluoro-4-(1H-pyrazol-5-yl)benzonitrile hydrochloride (201 mmol, 51.8 g) was dissolved in THF (510 ml). Sodium hydroxide 50% (401 mmol, 32.1 g) was added and the resulting mixture was stirred at RT for 3 h. Almost all the solvents were evaporated and water was added to the residue. The mixture was stirred overnight at RT. The precipitate was removed by filtration the solid was flushed twice with water. The solid was dried under vacuum. 35.8 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 7.05 (d, 1H), 7.88-7.97 (m, 2H), 8.02-8.07 (m, 1H), 13.37 (bs, 1H).