Cesium carbonate → 4-Fluoro-4'-hydroxybiphenyl

HRID 1377917Notes

Reaction equation

HRID 1377917 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 108944-IodophenolHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 3454204-Fluoro-4'-hydroxybiphenylYield 46.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture under N2 in DMF (18 mL) of 4-iodophenol (2.00 g, 9.09 mmol), 4-fluorophenylboronic acid (1.40 g, 10.0 mmol), cesium carbonate (4.44 g, 13.6 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.27 g, 0.23 mmol) was stirred for 10 minutes at ambient temperature and then overnight at reflux. The reaction mixture was cooled to ambient temperature, diluted with ethyl acetate, and extracted twice with water. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Chromatography on silica gel (10:1, then 5:1 hexanes-ethyl acetate) gave 4-(4-fluorophenyl)phenol (0.79 g, 46%) as a white powder.

Workup

  1. temperatureovernight at reflux
  2. extractionextracted twice with water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d231b41ed7d4dc1a914ecab9366b1d6
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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