Cesium carbonate → HCID 86704958, compound

HRID 2170216Notes

Reaction equation

HRID 2170216 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[CH:5]=[O:6].[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[OH:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:19][C:13]1[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=1[F:11])[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 86704958HCID 86704958, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-4-fluorobenzaldehyde (4.06 g, 20.0 mmol), 2,4-difluorophenol (2.60 g, 20.0 mmol) and cesium carbonate (7.17 g, 22.0 mmol) in dimethyl sulfoxide (20 mL) was heated at 100° C. for 1 hour. The reaction mixture was partitioned with ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride twice, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 20% ethyl acetate in heptanes) to provide the title compound (5.94 g, 95%).

Workup

  1. customThe reaction mixture was partitioned with ethyl acetate and water
  2. washThe organic layer was washed with saturated aqueous sodium chloride twice
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica gel, 20% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-f699a33584be4d39b527919f2a9bba2a
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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