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

HRID 660241Notes

Reaction equation

HRID 660241 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-7038a89078124ac6abb75b6cb3bafafb
Source dataset
uspto-grants-2011_12
Patent number
US08084476B2

Reaction notes

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