Cesium carbonate → HCID 89479687, compound

HRID 589250Notes

Reaction equation

HRID 589250 reaction equation
Cl/[CH:2]=[C:3](/[C:13]1[S:14][C:15]([CH3:18])=[CH:16][CH:17]=1)\[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1.[F-].[Cs+].C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O(C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][O:11][C:7]1[CH:8]=[CH:9][C:10]2[CH:2]=[C:3]([C:13]3[S:14][C:15]([CH3:18])=[CH:16][CH:17]=3)[O:4][C:5]=2[CH:6]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 25953Cesium fluorideHCID 89479577HCID 89479577, compound

Product 1

HCID 89479687HCID 89479687, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 4285986Bis[2-(diphenylphosphino)phenyl] etherCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

(Z)-2-(2-chloro-1-(3-methoxyphenoxy)vinyl)-5-methylthiophene (97) (4.7 g, 16.74 mmol), Pd2 dba3 (0.178 g, 0.399 mmol), (oxybis(2,1-phenylene))bis(diphenylphosphine) (0.429 g, 0.797 mmol), cesium fluoride (7.27 g, 47.8 mmol) and cesium carbonate (15.58 g, 47.8 mmol) were placed into a 250-mL three-neck rbf, sealed with a septum and purged with argon for 20-30 minutes. 100 mL dioxane was added. The solution was vigorously stirred and brought to reflux for 18 hours and cooled. The layers were separated and the aqueous layer was extracted with DCM once more. The combined organic layers were washed with brine, dried with anhydrous MgSO4, filtered and concentrated. The product was purified by column to provide (98) (3.38 g, 13.83 mmol, 87% yield).

Workup

  1. customrbf, sealed with a septum
  2. custompurged with argon for 20-30 minutes
  3. addition100 mL dioxane was added
  4. temperatureto reflux for 18 hours
  5. temperaturecooled
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with DCM once more
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried with anhydrous MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe product was purified by column

Sources & evidence

ORD record
ord-b59ca9c5a8bb4425b6246ca2d89ef539
Source dataset
uspto-grants-2016_01
Patent number
US09227986B2

Reaction notes

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