Cesium carbonate → HCID 46314341, compound

HRID 1619678Notes

Reaction equation

HRID 1619678 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.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.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:19][C:13]1[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:12]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27339863-Fluorophenylboronic acidHCID 70181824-Bromo-3-chlorophenol

Product 1

HCID 46314341HCID 46314341, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

3-Fluorobenzeneboronic acid (405 mg, 2.89 mmol) and 4-bromo-3-chlorophenol (500 mg, 2.41 mmol) were dissolved in dioxane (15 mL) and water (3 mL) and the solution degassed. Tetrakis(triphenylphosphine) palladium (0) (278 mg, 0.24 mmol) was added followed by caesium carbonate (2.36 g, 7.23 mmol) and the reaction was stirred at 80° C. under nitrogen for 18 hours. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (20% ethyl acetate in heptane) to afford the title compound (509 mg, 95%) as a colourless oil.

Workup

  1. customwater (3 mL) and the solution degassed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custompartitioned between ethyl acetate and water
  4. customThe aqueous layer was separated
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel column chromatography (20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-26e3ee54eed2428e80feb5b2902b3c8f
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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