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

HRID 2271459Notes

Reaction equation

HRID 2271459 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]=238.09240.09.

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-6892268d82df4041832238829405907f
Source dataset
uspto-grants-2015_09
Patent number
US09120770B2

Reaction notes

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