Water → 2-Methyl-5-nitrobenzotrifluoride

HRID 1926595Notes

Reaction equation

HRID 1926595 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].[F:12][C:13]([F:18])([F:17])C([O-])=O.[Na+].O>CN1C(=O)CCC1>[F:12][C:13]([F:18])([F:17])[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 821892-Bromo-4-nitrotolueneHCID 517019Sodium Trifluoroacetate

Product 1

HCID 27754472-Methyl-5-nitrobenzotrifluorideYield 65.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 2-bromo-4-nitrotoluene (23.2 mmol) in NMP (200 mL) was added sodium trifluoroacetate (8.5 g, 62.5 mmol) and Cul (8.75 g, 46 mmol) and the reaction mixture was stirred at 160° C. for 4 hours. The solution was cooled and water (300 mL) was added. The solution was filtrated and the solid was washed with ethyl ether (250 mL×3). The organic phase was washed with water and brine, dried, filtered, concentrated and purified through column chromatography to give 2-(trifluoromethyl)-4-nitrotoluene (3.12 g).

Workup

  1. temperatureThe solution was cooled
  2. filtrationThe solution was filtrated
  3. washthe solid was washed with ethyl ether (250 mL×3)
  4. washThe organic phase was washed with water and brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified through column chromatography

Sources & evidence

ORD record
ord-5ab5260c13534dd2aaecce4d47c2089f
Source dataset
uspto-grants-2012_05
Patent number
US08183242B2

Reaction notes

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