m-Chloroperbenzoic acid → 4-Chloro-3-fluoropyridine 1-oxide
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe reaction mixture was quenched with 10% aq. Na2S2O3
- extractionThe aq. phase was extracted with EA (6×)
- dry with materialphase was dried over MgSO4
- customevaporated to dryness
- 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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