Water → 2-Chloro-4'-fluorobiphenyl-4-ol

HRID 1619682Notes

Reaction equation

HRID 1619682 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=1[Cl:19].O.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:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2856454-Fluorophenylboronic acidHCID 70181824-Bromo-3-chlorophenol

Product 1

HCID 463143422-Chloro-4'-fluorobiphenyl-4-olYield 94%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

4-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) under nitrogen. The solution was degassed before 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. for 18 hours. The cooled reaction mixture was 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 (503 mg, 94%) as a tan oil which solidified on standing.

Workup

  1. additionwas added
  2. customThe cooled reaction mixture
  3. customwas partitioned 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-30599fcb75374c4d8e09d49071735ca9
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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