m-Chloroperbenzoic acid → Methyl 5-fluoro-2-methylnicotinate 1-oxide

HRID 493561Notes

Reaction equation

HRID 493561 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].ClC1C=C(C(OO)=[O:21])C=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[N+:4]([O-:21])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68863106Methyl 5-fluoro-2-methylnicotinate

Product 1

HCID 68862688Methyl 5-fluoro-2-methylnicotinate 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of methyl 5-fluoro-2-methylnicotinate (step 2, 936 mg, 5.53 mmol) in dichloromethane (100 ml) was added 3-chlorobenzenecarboperoxoic acid (2.38 g, 13.8 mmol) and the reaction suspension was stirred overnight at room temperature. The reaction was quenched by the addition of sat. sodium thiosulfate solution and sat. sodium bicarbonate solution was added. The whole mixture was extracted with dichloromethane. The organic phase was dried over sodium sulfate and concentrated to afford 1.12 g (quant.) of title compound:

Workup

  1. customThe reaction was quenched by the addition of sat. sodium thiosulfate solution and sat. sodium bicarbonate solution
  2. additionwas added
  3. extractionThe whole mixture was extracted with dichloromethane
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2f40ccd447174825a70fc74fa034b052
Source dataset
uspto-grants-2009_05
Patent number
US07534914B2

Reaction notes

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