Nitric Acid → HCID 89649315, compound

HRID 530265Notes

Reaction equation

HRID 530265 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]([F:20])([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[C:7]([N:9]([CH3:11])[CH3:10])=[O:8]>>[F:20][C:6]([F:5])([O:12][C:13]1[CH:14]=[C:15]([F:19])[C:16]([N+:1]([O-:4])=[O:2])=[CH:17][CH:18]=1)[C:7]([N:9]([CH3:11])[CH3:10])=[O:8]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 89649428HCID 89649428, compound

Product 1

HCID 89649315HCID 89649315, compoundYield 28%

Procedure

Nitric acid (100%, 200 mL, 4.8 mol) was cooled to −5° C. 2,2-Difluoro-2-(3-fluoro-phenoxy)-N,N-dimethyl-acetamide (19.0 g, 81.5 mmol) was added at rate to keep the temperature below −2° C. Upon complete addition stirring was continued for 30 min. The reaction mixture was then poured on 450 mg ice-water. The aqueous phase was extracted with TBME (3×100 mL); the combined organic phases were washed with water (100 mL) and brine (100 mL) and dried over MgSO4. Evaporation of the solvent gave the crude product that was purified by preparative HPLC. The product (6.5 g, >98% by HPLC, 28% yield) was obtained as a yellow solid.

Workup

  1. customthe temperature below −2° C
  2. additionUpon complete addition
  3. extractionThe aqueous phase was extracted with TBME (3×100 mL)
  4. washthe combined organic phases were washed with water (100 mL) and brine (100 mL)
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e11c0bc3b2af4c67bf0200d8166de15f
Source dataset
uspto-grants-2016_05
Patent number
US09353070B2

Reaction notes

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