Acetic Acid → 2-Fluoro-4-methyl-6-nitrophenol

HRID 17284Notes

Reaction equation

HRID 17284 reaction equation
[N+:1]([O-:4])(O)=[O:2].C(O)(=O)C.[F:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[OH:17]>O>[F:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([N+:1]([O-:4])=[O:2])[C:11]=1[OH:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 27784852-Fluoro-4-methylphenol

Product 1

HCID 227538152-Fluoro-4-methyl-6-nitrophenolYield 38.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

70% Nitric acid (d=1.42) (5.5 ml, 87.4 mmol) was dropwise added to an acetic acid (105 ml) solution of 2-fluoro-4-methyl-phenol (10.5 g, 83.2 mmol), taking 20 minutes, followed by stirring at room temperature for 30 minutes. Water was added to the reaction liquid, followed by extraction three times with diethyl ether, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with n-hexane:ethyl acetate (10:1) was concentrated under reduced pressure to obtain the entitled compound (5.47 g, 31%) as a yellow solid.

Workup

  1. extractionfollowed by extraction three times with diethyl ether
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration and concentration under reduced pressure
  5. concentrationthe eluate with n-hexane:ethyl acetate (10:1) was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e1ec134b539f42d393827d72b1772b35
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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