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

HRID 2048087Notes

Reaction equation

HRID 2048087 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>[F:14][CH:10]([F:15])[O:8][C:7]1[C:2]([Br:1])=[N:3][CH:4]=[CH:5][CH:6]=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 separated, 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 separated
  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-06f9670d354548f393fca1b2a1dd6f08
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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