Sodium Hydroxide → 2-chloro-6-fluoro-4-(1H-pyrazol-3-yl)benzonitrile

HRID 1409311Notes

Reaction equation

HRID 1409311 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

Reactant 2

HCID 14798Sodium HydroxideHCID 709807222-Chloro-6-fluoro-4-(1H-pyrazol-5-yl)benzonitrile hydrochloride

Product 1

HCID 671697812-chloro-6-fluoro-4-(1H-pyrazol-3-yl)benzonitrileYield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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).

Workup

  1. customAlmost all the solvents were evaporated
  2. additionwater was added to the residue
  3. stirringThe mixture was stirred overnight at RT
  4. customThe precipitate was removed by filtration the solid
  5. customwas flushed twice with water
  6. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-5ad683de8ee8439bae3d68b9104896b2
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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