Cesium carbonate → HCID 46314340, compound

HRID 1619685Notes

Reaction equation

HRID 1619685 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.Br[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=1[Cl:19].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.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]>[Cl:19][C:13]1[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:12]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27343542-Fluorophenylboronic acidHCID 70181824-Bromo-3-chlorophenol

Product 1

HCID 46314340HCID 46314340, compoundYield 82.9%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Fluorophenylboronic acid (0.405 g, 2.89 mmol) and 4-bromo-3-chlorophenol (0.500 g, 2.41 mmol) were dissolved in dioxane (10 mL). A solution of caesium carbonate (2.35 g, 7.21 mmol) in water (2 mL) was added and the reaction mixture was degassed. Tetrakis(triphenylphosphine)palladium (0) (0.280 g, 0.242 mmol) was added and reaction was further degassed before heating the reaction at 100° C. for 18 hours. The cooled reaction mixture was filtered through a pad of celite. The filtrate was diluted with EtOAc and washed with water and dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by flash chromatography on silica gel eluting with EtOAc/Heptane 2:3 to give the title compound (0.445 g, 69%) as dark solid

Workup

  1. customthe reaction mixture was degassed
  2. customreaction
  3. customwas further degassed
  4. temperaturebefore heating
  5. customthe reaction at 100° C. for 18 hours
  6. customThe cooled reaction mixture
  7. filtrationwas filtered through a pad of celite
  8. additionThe filtrate was diluted with EtOAc
  9. washwashed with water
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customevaporated in vacuo
  13. customThe residue was purified by flash chromatography on silica gel eluting with EtOAc/Heptane 2:3

Sources & evidence

ORD record
ord-cd50d6afed5447ffa84595d8bd5acd58
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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