m-Chloroperbenzoic acid → HCID 90214903, compound

HRID 1480196Notes

Reaction equation

HRID 1480196 reaction equation
[F:1][C:2]1([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:11]=2[O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[CH2:5][CH2:4][CH2:3]1.C1C=C(Cl)C=C(C(OO)=[O:26])C=1>ClCCl>[F:1][C:2]1([C:6]2[CH:7]=[N+:8]([O-:26])[CH:9]=[CH:10][C:11]=2[O:12][CH2:13][C:14]([F:15])([F:16])[F:17])[CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 90204253HCID 90204253, compound

Product 1

HCID 90214903HCID 90214903, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(1-fluorocyclobutyl)-4-(2,2,2-trifluoroethoxy)pyridine (example 127a, 1.68 g, 6.74 mmol) in dichloromethane (40 ml) was added m-CPBA (3.49 g, 10.1 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was transferred into a separatory funnel and extracted with a 2M aqueous solution of sodium carbonate. The organic phase was collected and the aqueous phase was back-extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated down to dryness to yield the crude title compound (1.68 g, 94%) which was used without any purification for the next step; MS (ESI, m/z): 266.5 (M+H+).

Workup

  1. customThe reaction mixture was transferred into a separatory funnel
  2. extractionextracted with a 2M aqueous solution of sodium carbonate
  3. customThe organic phase was collected
  4. extractionthe aqueous phase was back-extracted with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customevaporated down to dryness

Sources & evidence

ORD record
ord-86f37fb9100b42209393fc918b45eb9a
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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