Water → HCID 57423924, compound

HRID 2064083Notes

Reaction equation

HRID 2064083 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[H-].[Na+].O([CH2:22][C:23]([F:26])([F:25])[F:24])S(C(F)(F)F)(=O)=O.O>CN(C)C=O.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[C:4]([O:11][CH2:22][C:23]([F:26])([F:25])[F:24])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 57423924HCID 57423924, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A stirred solution of 3-fluoro-4-nitrophenol (200 mg, 1.3 mmol) in dimethylformamide (3 ml) at 0° C. under argon was treated portionwise with sodium hydride (60 mg of 60% oil dispersion, 1.5 mmol) and maintained for 20 minutes. The mixture was treated with trifluoroethyl triflate (325 mg, 1.4 mmol), then allowed to warm to room temperature and stir overnight. The yellow solution was treated with water (40 ml) and brine (5 ml) and extracted with ethyl acetate. The extract was washed with water, dried (Na2SO4) and concentrated under vacuum to leave the title compound as a yellow oil (280 mg, 92%).

Workup

  1. temperaturemaintained for 20 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-bef7f965aead482a8d8cd69439b7f05c
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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