4-Nitrophenol → 1-Nitro-4-(2,2,2-trifluoroethoxy)benzene

HRID 2248157Notes

Reaction equation

HRID 2248157 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].CS(O[CH2:18][C:19]([F:22])([F:21])[F:20])(=O)=O>CN(P(N(C)C)(N(C)C)=O)C>[F:20][C:19]([F:22])([F:21])[CH2:18][O:12][C:9]1[CH:10]=[CH:11][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 24758Sodium hydrideHCID 5565652,2,2-Trifluoroethyl Methanesulfonate

Product 1

HCID 27757691-Nitro-4-(2,2,2-trifluoroethoxy)benzene

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent4×

Procedure

To prewashed sodium hydride (0.61 g, 25.5 mmol) in 10 ml of hexamethylphosphorotriamide (HMPT) is added 4-nitrophenol (3.55 g, 25.5 mmol) in 10 ml of HMPT at 25°-30°. Five ml more of HMPT is added and the mixture is warmed gently to 45°-50° for 30 min. 2,2,2-Trifluoroethyl methansulfonate (5.0 g, 28.0 mmol) and HMPT (1 ml) are then added and the mixture is heated to 146°-151° for 20 hours. The reaction mixture is cooled to RT and is then poured into ice water and extracted with ether (3X). The combined ether layers are washed with water and brine, dried, filtered and rotoevaporated to give 4-(2,2,2-trifluoroethoxy)nitrobenzene.

Workup

  1. temperaturethe mixture is warmed gently to 45°-50° for 30 min
  2. temperaturethe mixture is heated to 146°-151° for 20 hours
  3. extractionextracted with ether (3X)
  4. washThe combined ether layers are washed with water and brine
  5. customdried
  6. filtrationfiltered

Sources & evidence

ORD record
ord-5beb19f3c9a9400b8904a1cbc007283f
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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