4-Nitrophenol → 4-(Difluoromethoxy)nitrobenzene

HRID 3018

Reaction equation

HRID 3018 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:12]([F:17])([F:16])C([O-])=O.[Na+].[OH-].[Na+]>CN(C=O)C.O>[F:16][CH:12]([F:17])[O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 14798Sodium HydroxideHCID 2734985Sodium chlorodifluoroacetate

Product 1

HCID 27370144-(Difluoromethoxy)nitrobenzeneYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

4-Nitrophenol (0.10 g, 0.72 mmol, Aldrich), sodium chlorodifluoroacetate (0.11 g, 0.72 mmol, Alfa Products) and sodium hydroxide (0.03 g, 0.72 mmol) were combined in dry DMF (1 mL) under an atmosphere of argon. After stirring at 125° C. for 1 h, the mixture was cooled to RT, was diluted with water and was extracted twice with ether. The combined organic extracts were washed twice with brine, were dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes ) to provide the title compound as a white solid (0.10 g, 73%). mp 33°-35° C.

Workup

  1. temperaturethe mixture was cooled to RT
  2. extractionwas extracted twice with ether
  3. washThe combined organic extracts were washed twice with brine
  4. dry with materialwere dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes )

Sources & evidence

ORD record
ord-b2d252a75b1947e3893ae5090ef4d0e4
Source dataset
uspto-grants-1998_03
Patent number
US05731477

Linked notes

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