m-Chloroperbenzoic acid → 6-Bromo-3-fluoro-2-methylpyridine 1-oxide

HRID 1258555Notes

Reaction equation

HRID 1258555 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([F:9])=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:18])C=1.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[N+:7]([O-:18])=[C:6]([CH3:8])[C:5]([F:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 27831806-Bromo-3-fluoro-2-methylpyridineHCID 22607107sodium thiosulfate NaHCO3

Product 1

HCID 866531136-Bromo-3-fluoro-2-methylpyridine 1-oxideYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 6-bromo-3-fluoro-2-methylpyridine (2.84 g, 14.94 mmol, 1 eq.) was dissolved in DCM (250 ml) and cooled to 0° C. Then mCPBA (7.34 g, 29.89 mmol, 2 eq.) was added by portions and the reaction was warmed to r.t. and stirred for 48 h. A sat. aqueous solution of NaHCO3/Na2S2O3 (1/1) was added and stirring allowed for 5 min. Then DCM was added and the layers separated. The aqueous layer was extracted with DCM then the organics were combined, dried over MgSO4 and concentrated. 6-bromo-3-fluoro-2-methylpyridine 1-oxide (2.94 g, 89%) was obtained as a white solid.

Workup

  1. temperaturethe reaction was warmed to r.t.
  2. stirringstirring
  3. waitallowed for 5 min
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted with DCM
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-620ae8e3d6f74b5b9a81f51003097f2c
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

Loading…