Sodium Hydroxide → 1-[2,3-Difluoro-4-(5-fluoropyridin-2-yl)phenyl]-2,2-difluoroethanone

HRID 216343Notes

Reaction equation

HRID 216343 reaction equation
[OH-].[Na+].[F:3][C:4]1[C:9]([F:10])=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=2)[CH:7]=[CH:6][C:5]=1[C:18](=[O:30])[C:19](P(=O)(OCC)OCC)([F:21])[F:20]>CO>[F:3][C:4]1[C:9]([F:10])=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=2)[CH:7]=[CH:6][C:5]=1[C:18](=[O:30])[CH:19]([F:21])[F:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86638498HCID 86638498, compound

Product 1

HCID 591619891-[2,3-Difluoro-4-(5-fluoropyridin-2-yl)phenyl]-2,2-difluoroethanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 M Aqueous sodium hydroxide (1 mL, 1 mmol) was added to a solution of diethyl {2-[2,3-difluoro-4-(5-fluoropyridin-2-yl)phenyl]-1,1-difluoro-2-oxoethyl}phosphonate (872 mg, 2 mmol) in methanol (8 mL) at room temp. After stirring at rt for 30 min, the reaction was quenched with 1 N hydrochloric acid. The reaction mixture was extracted with ethyl acetate washed with saturated aqueous sodium bicarbonate and brine, dried (sodium sulfate) and concentrated. Chromatography over silica eluting with 0-60% ethyl acetate/hexane afforded the title compound as a white solid.

Workup

  1. customthe reaction was quenched with 1 N hydrochloric acid
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washwashed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2bbae4e2b6014247816e944a5efe89d8
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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