m-Chloroperbenzoic acid → 4-Chloro-3-fluoro-pyridine 1-oxide

HRID 418054Notes

Reaction equation

HRID 418054 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[F:19]>C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][N+:16]([O-:9])=[CH:15][C:14]=1[F:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 38524294-Chloro-3-fluoropyridine

Product 1

HCID 215698534-Chloro-3-fluoro-pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MCPBA (28.1 g) was added to a solution of 4-chloro-3-fluoro-pyridine (10.0 g) in DCM (150 ml) and the reaction mixture stirred for 60 h at RT. The reaction mixture was quenched with 10% aq. Na2S2O3 and the basicity of the aq. phase adjusted with aq. sat. Na2CO3 to pH 9. The aq. phase was extracted with EA (6×), and the combined org. phase was dried over MgSO4 and evaporated to dryness. The desired compound (8.4 g) was used in the next step without further purification.

Workup

  1. customThe reaction mixture was quenched with 10% aq. Na2S2O3
  2. extractionThe aq. phase was extracted with EA (6×)
  3. dry with materialphase was dried over MgSO4
  4. customevaporated to dryness
  5. customThe desired compound (8.4 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-7b0b97b2ff0b46f3a7997c171a9aa9f8
Source dataset
uspto-grants-2012_01
Patent number
US08093250B2

Reaction notes

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