Cesium carbonate → 2-broMo-3-(difluoroMethoxy)pyridine

HRID 512073Notes

Reaction equation

HRID 512073 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[C:10]([F:15])([F:14])C([O-])=O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Br:1][C:2]1[C:7]([O:8][CH:10]([F:15])[F:14])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 230702-Bromo-3-pyridinolHCID 2734985Sodium chlorodifluoroacetate

Product 1

HCID 580424482-broMo-3-(difluoroMethoxy)pyridineYield 35.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromo-3-pyridinol (1.26 g, 7.23 mmol) in DMF (35 mL) and water (5 mL) was added sodium chlorodifluoroacetate (2.93 g, 18.1 mmol) followed by cesium carbonate (4.71 g, 14.5 mmol). The reaction was heated to 100° C. for 36 hours before partitioning between EtOAc and water. The organic layer was collected, dried over magnesium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with EtOAc:heptane 1:3 to afford the title compound as a colourless oil (570 mg, 35%).

Workup

  1. custombefore partitioning between EtOAc and water
  2. customThe organic layer was collected
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. washeluting with EtOAc:heptane 1:3

Sources & evidence

ORD record
ord-2e4d28557e22415e9b773334eea93f67
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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