Water → 3-Bromo-2-(difluoromethoxy)-5-methylpyridine

HRID 578818Notes

Reaction equation

HRID 578818 reaction equation
[Br:1][C:2]1[C:3]([OH:9])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:10][C:11]([F:19])(S(F)(=O)=O)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].O>C(#N)C>[Br:1][C:2]1[C:3]([O:9][CH:11]([F:19])[F:10])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 178430683HCID 178430683, compound

Product 1

HCID 904150763-Bromo-2-(difluoromethoxy)-5-methylpyridineYield 71.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-bromo-5-methylpyridin-2-ol (25.0 g, 0.13 mol) in ACN (100 mL) was added 2,2-difluoro-2-(fluorosulfonyl)acetic acid (23.7 g, 0.13 mol) and sodium carbonate (28.2 g, 0.270 mol). The reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the reaction mixture was extracted with DCM. The combined organic layers were dried (Na2SO4), and the solvent was removed under reduced pressure. Purification (FCC, SiO2, 0-10%, EtOAc/hexanes) afforded the title compound as an off-white solid (22 g, 70%). M+H]=238.09/240.09.

Workup

  1. extractionthe reaction mixture was extracted with DCM
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. customthe solvent was removed under reduced pressure
  4. customPurification (FCC, SiO2, 0-10%, EtOAc/hexanes)

Sources & evidence

ORD record
ord-12aeb3dfb9cb42a7816848d2b508c726
Source dataset
uspto-grants-2015_05
Patent number
US09040692B2

Reaction notes

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