m-Chloroperbenzoic acid → 3-Cyano-5-(3,5-difluorobenzyloxy)pyridine 1-oxide

HRID 334414Notes

Reaction equation

HRID 334414 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:14]=[C:15]([CH:26]=[C:27]([F:29])[CH:28]=1)[CH2:16][O:17][C:18]1[CH:19]=[N:20][CH:21]=[C:22]([CH:25]=1)[C:23]#[N:24]>C(#N)C>[C:23]([C:22]1[CH:21]=[N+:20]([O-:9])[CH:19]=[C:18]([O:17][CH2:16][C:15]2[CH:26]=[C:27]([F:29])[CH:28]=[C:13]([F:12])[CH:14]=2)[CH:25]=1)#[N:24]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 682765335-(3,5-Difluorobenzyloxy)nicotinonitrile

Product 1

HCID 682764423-Cyano-5-(3,5-difluorobenzyloxy)pyridine 1-oxideYield 75.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

224 mg of m-CPBA is added at 0° C. to a solution in acetonitrile of 250 mg of 5-(3,5-difluorobenzyloxy)nicotinonitrile. The reaction medium is stirred for 20 hours while a precipitate is formed progressivelt. This solid is then filtered and washed to yield 200 mg (75%) of 3-cyano-5-(3,5-difluorobenzyloxy)pyridine 1-oxide in the form of a white powder.

Workup

  1. customis formed progressivelt
  2. filtrationThis solid is then filtered
  3. washwashed

Sources & evidence

ORD record
ord-d0087d435e954b02b0173f4f2eee3ac3
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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