Dimethylformamide → 2-Bromo-5-(difluoromethoxy)pyridine

HRID 15044

Reaction equation

HRID 15044 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]([F:13])([F:12])C([O-])=O.[Na+].CN(C=O)C.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][N:22]=1>CCOCC>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:8]([F:12])[F:13])=[CH:23][N:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 231205792-Bromo-5-(difluoromethoxy)pyridineYield 43%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (2.4 g, 17.3 mmols) and sodium chlorodifluoroacetate (4.2 g, 27.5 mmols) were added to a DMF (20 mL) solution of 2-bromo-5-hydroxypyridine (2.4 g, 13.8 mmols) and stirred overnight at 80° C. The reaction liquid was cooled to room temperature, added ether, washed with water and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the resulting residue was purified on silica gel column chromatography (C-300; hexane:ethyl acetate=100:1-100:2) to provide the title compound (1.32 g, 43%).

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationConcentrating the solvent under reduced pressure
  6. customthe resulting residue was purified on silica gel column chromatography (C-300; hexane:ethyl acetate=100:1-100:2)

Sources & evidence

ORD record
ord-a7269e992a824e05b5d1f6a6b677604a
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Linked notes

Loading…