Potassium Phosphate, Dibasic → 1-(2-Fluoro-4-nitro-phenyl)-4-methyl-[1,2,3]-triazole

HRID 1452576Notes

Reaction equation

HRID 1452576 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][NH:5][CH:6]=1.OP([O-])([O-])=O.[K+].[K+].[F:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1F>CN(C=O)C>[F:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1[N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[N:4]1

Participants

5

Reactant 3

HCID 24450Potassium Phosphate, DibasicHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 1784309184-methyl-1H-1,2,3-triazole

Product 1

HCID 575269881-(2-Fluoro-4-nitro-phenyl)-4-methyl-[1,2,3]-triazoleYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-methyl-[1,2,3]-triazole (60 g, 0.72 mol), K2HPO4 (250 g, 1.44 mol) and 3,4-difluoronitrobenzene (80 ml, 0.723 mol) in DMF (3.4 litres) was stirred at 85° C. under N2 for 2.5 days. After removal of DMF in vacuo, the residue was chromatographed on silica gel with 0-5% ethyl acetate in dichloromethane to give the title compound as a light yellow solid (38.3 g, 24%). The other two isomers were also isolated.

Workup

  1. customAfter removal of DMF in vacuo
  2. customthe residue was chromatographed on silica gel with 0-5% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-0a4ccd04f79a4ba5ab04d9f7a8faf7cc
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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