Nitric Acid → 2-Nitro-6-(trifluoromethyl)phenol

HRID 501547Notes

Reaction equation

HRID 501547 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[N+:12]([O-])([OH:14])=[O:13]>CC(O)=O>[N+:12]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[C:4]=1[OH:9])([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 679582-Trifluoromethylphenol

Product 1

HCID 9018342-Nitro-6-(trifluoromethyl)phenolYield 44%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of commercially available 2-trifluoromethylphenol (2.5 g, 15.42 mmol) in AcOH (3 mL) cooled to 0° C. was added dropwise concentrated HNO3 (1.5 mL). After the addition, the mixture was stirred at 0° C. for 5 min, at rt for 10 min, then poured into ice/water, and extracted with ether (3×). The combined ether extracts were washed with water, brine, dried (Na2SO4) and concentrated under reduced pressure. The residue was chromatographed (silica gel) eluting with 0% to 10% EtOAc/hexane to yield the title compound (1.4 g, 44% yield).

Workup

  1. additionAfter the addition
  2. extractionextracted with ether (3×)
  3. washThe combined ether extracts were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed (silica gel)
  7. washeluting with 0% to 10% EtOAc/hexane

Sources & evidence

ORD record
ord-97f1671f846740bc8f56d11530e8d1d9
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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