m-Chloroperbenzoic acid → HCID 90203464, compound

HRID 1480167Notes

Reaction equation

HRID 1480167 reaction equation
[CH:1]1([C:5]2[CH:6]=[N:7][CH:8]=[CH:9][C:10]=2[O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[CH2:4][CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:22]>ClCCl>[CH:1]1([C:5]2[CH:6]=[N+:7]([O-:22])[CH:8]=[CH:9][C:10]=2[O:11][CH2:12][C:13]([F:16])([F:14])[F:15])[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 90203676HCID 90203676, compound

Product 1

HCID 90203464HCID 90203464, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-cyclobutyl-4-(2,2,2-trifluoroethoxy)pyridine (Example 108c, 3.81 g, 16.5 mmol) in dichloromethane (100 ml) was added 3-chloroperoxybenzoic acid (5.54 g, 24.7 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was transferred into a separatory funnel and extracted with an 2.0M aqueous solution of sodium carbonate. The organic phase was collected and the aqueous phase was back-extracted with dichloromethane. The organic phases were combined, dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient to yield the title compound (3.52 gr, 82%) as a white solid. MS (ESI, m/z): 248.5 (M+H+).

Workup

  1. customThe reaction mixture was transferred into a separatory funnel
  2. extractionextracted with an 2.0M aqueous solution of sodium carbonate
  3. customThe organic phase was collected
  4. extractionthe aqueous phase was back-extracted with dichloromethane
  5. dry with materialdried over sodium sulfate
  6. customevaporated down to dryness
  7. customThe crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient

Sources & evidence

ORD record
ord-106ba70ce0fd444e8b9d5dcec7b25e0d
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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