p-Fluoronitrobenzene → Nitro-4-(2,2,2-trifluoro-1-methyl-ethoxy)-benzene

HRID 2381159Notes

Reaction equation

HRID 2381159 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[F:11][C:12]([F:17])([F:16])[CH:13]([OH:15])[CH3:14].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:15][CH:13]([CH3:14])[C:12]([F:17])([F:16])[F:11])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 97741,1,1-Trifluoro-2-propanolHCID 10796Cesium carbonate

Product 1

HCID 66577895Nitro-4-(2,2,2-trifluoro-1-methyl-ethoxy)-benzeneYield 95.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-fluoro-4-nitro-benzene (4.24 g) and (rac)-1,1,1-trifluoro-propan-2-ol (4.563 g) in acetonitile (50 ml) under an argon atmosphere was added at RT Cs2CO3 (13.04 g) and the mixture was refluxed for 10 h. It was then acidified with diluted aqueous HCL and partitioned between ethyl acetate and water. The layers were separated, dried over Na2SO4 and the solvent was then evaporated off to give (rac)-1-nitro-4-(2,2,2-trifluoro-1-methyl-ethoxy)-benzene as brown oil (6.74 g) that was used without further purification.

Workup

  1. temperaturethe mixture was refluxed for 10 h
  2. custompartitioned between ethyl acetate and water
  3. customThe layers were separated
  4. dry with materialdried over Na2SO4
  5. customthe solvent was then evaporated off

Sources & evidence

ORD record
ord-760b9606c1cc434d9867470cb9e9bc16
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

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