Tert-Butyl nitrite → HCID 23359008, compound

HRID 2396958Notes

Reaction equation

HRID 2396958 reaction equation
N(OC(C)(C)C)=O.[F:8][C:9]1[C:15]([CH3:16])=[C:14]([F:17])[C:13]([F:18])=[C:12]([N+:19]([O-:21])=[O:20])[C:10]=1N>CN(C)C=O>[F:17][C:14]1[C:13]([F:18])=[C:12]([N+:19]([O-:21])=[O:20])[CH:10]=[C:9]([F:8])[C:15]=1[CH3:16]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 23359009HCID 23359009, compound

Product 1

HCID 23359008HCID 23359008, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of t-butyl nitrite (1.87 g) in anhydrous dimethylformamide (10.9 ml) is added dropwise a solution of 2,4,5-trifluoro-3-methyl-6-nitroaniline (2.05 g) in anhydrous dimethylformamide (16.4 ml) with stirring at 50°-52° C. and the mixture is stirred at the same temperature for 30 minutes. After cooling, the reaction mixture is poured into ice-water, extracted with diethyl ether, and the extract is washed with water and dried. The solvent is distilled off under reduced pressure and the obtained residue is purified by silica-gel column-chromatography (eluent; dichloromethane : n-hexane=1 : 4) to give 2,3,6-trifluoro-4-nitrotoluene (0.7 g).

Workup

  1. stirringthe mixture is stirred at the same temperature for 30 minutes
  2. temperatureAfter cooling
  3. extractionextracted with diethyl ether
  4. washthe extract is washed with water
  5. customdried
  6. distillationThe solvent is distilled off under reduced pressure
  7. customthe obtained residue is purified by silica-gel column-chromatography (eluent; dichloromethane : n-hexane=1 : 4)

Sources & evidence

ORD record
ord-9c82d4eb3685460193548010532e55f7
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

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