2,2,2-Trifluoroethanol → 4-Methyl-2-nitro-1-(2,2,2-trifluoroethoxy)benzene

HRID 1193476Notes

Reaction equation

HRID 1193476 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].Cl[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18]>CN(C=O)C>[CH3:16][C:13]1[CH:14]=[CH:15][C:10]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[C:11]([N+:17]([O-:19])=[O:18])[CH:12]=1

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 69764-Chloro-3-nitrotolueneHCID 24758Sodium hydride

Product 1

HCID 196228794-Methyl-2-nitro-1-(2,2,2-trifluoroethoxy)benzeneYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

2,2,2-Trifluoroethanol (60 g, 0.6 mol) was added dropwise to a stirred mixture of sodium hydride (12 g of a 60% dispersion, 0.3 mol) in 500 mL of DMF. After stirring for 20 minutes, 4-chloro-3-nitrotoluene (51.3 g, 0.3 mol) was added and the reaction heated at 150° C. for 16 hours. The reaction was cooled, poured into ice cold 5% HCl. The resulting precipitate was collected by filtration, dried to give 64 g of 5-methyl-2-(2,2,2-trifluoroethoxy)nitrobenzene.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationThe resulting precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-f6f87fabb4b1474e83e59ce3148413ff
Source dataset
uspto-grants-1989_03
Patent number
US04810699

Reaction notes

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