Cesium fluoride → HCID 57321084, compound

HRID 1375680Notes

Reaction equation

HRID 1375680 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16](I)[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[F-].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:8]=2)[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1

Participants

8

Reactant 4

HCID 25953Cesium fluorideHCID 80271Tri-o-tolylphosphineHCID 6401791-Iodo-3,5-dimethoxybenzeneHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 57321084HCID 57321084, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 600 mg (4.0 mmol) of 3-methoxyphenylboronic acid, 792 mg (3.0 mmol) of 3,5-dimethoxyiodobenzene, 34 mg (5 mol %) palladium(II)acetate, 182 mg (20 mol %) of tri-o-tolylphosphine, and 3.6 g (24 mmol) of cesium fluoride was added 10 mL of anhydrous dioxane. The reaction was stirred at reflux under N2 for 50 min, then poured into 30 mL of water and extracted with diethyl ether (3×10 mL). The combined ether layers were back extracted with saturated aqueous NaHCO3 solution (1×10 mL), then brine (1×10 mL), dried over MgSO4, filtered, and concentrated to an oil. This was purified via silica gel chromatography, eluting with 10%, ethyl acetate:hexanes to provide the titled compound (650 mg, 89%).

Workup

  1. temperatureat reflux under N2 for 50 min
  2. extractionextracted with diethyl ether (3×10 mL)
  3. extractionThe combined ether layers were back extracted with saturated aqueous NaHCO3 solution (1×10 mL)
  4. dry with materialbrine (1×10 mL), dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customThis was purified via silica gel chromatography
  8. washeluting with 10%, ethyl acetate

Sources & evidence

ORD record
ord-5e4d293691b540b58dd03e33712d8e9e
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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