Sulfuric Acid → 1-(3,5-Difluoropyridin-2-yl)ethan-1-one

HRID 1971449Notes

Reaction equation

HRID 1971449 reaction equation
[CH3:1][Mg]Br.[C:4]([C:6]1[C:11]([F:12])=[CH:10][C:9]([F:13])=[CH:8]N=1)#N.OS(O)(=O)=O.[NH4+:19].[OH-:20]>C(OCC)C.C1COCC1>[F:12][C:11]1[C:6]([C:4](=[O:20])[CH3:1])=[N:19][CH:8]=[C:9]([F:13])[CH:10]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 27832532-Cyano-3,5-difluoropyridineHCID 178418573HCID 178418573, compound

Product 1

HCID 552825761-(3,5-Difluoropyridin-2-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (10 ml of a 3N solution in diethylether) were added drop-wise with stirring to a solution of 15 g (10.71 mmol) 2-cyano-3,5-difluoropyridine in 100 ml THF at 0° C. and the mixture was subsequently stirred at room temperature until reaction was complete. For workup the mixture was acidified with 10% H2SO4 to pH 4, was subsequently made basic with 25% NH4OH, was extracted 2× with dichloromethane, and the combined organic phases were dried with MgSO4. Purification by chromatography on silica gel (dichloromethane/methanol 0-5%) yielded 500 mg of a light colored oil, which crystallized upon being left to stand.

Workup

  1. extractionwas extracted 2× with dichloromethane
  2. dry with materialthe combined organic phases were dried with MgSO4
  3. customPurification by chromatography on silica gel (dichloromethane/methanol 0-5%)

Sources & evidence

ORD record
ord-a3b222ff2e6549868527175f309073d3
Source dataset
uspto-grants-2013_04
Patent number
US08431604B2

Reaction notes

Loading…