Nitric Acid → HCID 57713304, compound

HRID 1983862Notes

Reaction equation

HRID 1983862 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[C:6]([OH:8])[CH:7]=1.[N+:13]([O-])([OH:15])=[O:14]>C(O)(=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([C:9]([F:10])([F:11])[F:12])[C:5]([N+:13]([O-:15])=[O:14])=[C:6]([OH:8])[CH:7]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 27375873-Fluoro-5-(trifluoromethyl)phenol

Product 1

HCID 57713304HCID 57713304, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

5-Fluoro-3-(trifluoromethyl)phenol (1.27 g) was dissolved in acetic acid (3 ml) and water (1.5 ml), and nitric acid (3.0 ml) was added thereto. The reaction mixture was stirred at 50° C. for 30 minutes. After cooling, water was added to the reaction mixture, and the mixture was extracted with ether. The extract was washed with an aqueous saturated sodium bicarbonate solution and water, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography (developing solution:ethyl acetate-hexane=1:3) to obtain the title compound as oil (0.33 g, 21%).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ether
  3. washThe extract was washed with an aqueous saturated sodium bicarbonate solution and water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (developing solution:ethyl acetate-hexane=1:3)

Sources & evidence

ORD record
ord-2e44993a4b5e42c7a7c5390c7f359712
Source dataset
uspto-grants-2009_06
Patent number
US07541478B2

Reaction notes

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