Cesium carbonate → HCID 86704958, compound

HRID 633580Notes

Reaction equation

HRID 633580 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 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
105 °C

Procedure

A suspension of 3-bromo-4-fluorobenzaldehyde (500 mg, 2.46 mmol), 2,4-difluorophenol (0.353 mL, 3.69 mmol) and cesium carbonate (1204 mg, 3.69 mmol) in dimethylsulfoxide (24 mL) was heated at 105° C. overnight. The reaction mixture was partitioned between ethyl acetate (200 mL) and 50% saturated aqueous sodium chloride (200 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×75 mL). The combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 2.5-100% ethyl acetate in heptanes) to afford the title compound (524 mg, 68% yield).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (200 mL) and 50% saturated aqueous sodium chloride (200 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×75 mL)
  4. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (silica gel, 2.5-100% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-cbe42c17d5a4481988cc68a4c7042b62
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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