1,3-Dibromobenzene → 3-Bromo-4'-fluorobiphenyl

HRID 724209Notes

Reaction equation

HRID 724209 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[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-].[Na+].[Na+]>CN(C=O)C>[Br:8][C:4]1[CH:3]=[C:2]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 79271,3-DibromobenzeneHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 27569773-Bromo-4'-fluorobiphenylYield 65.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1,3-dibromobenzene (25.3 g), 4-fluorophenylboronic acid (5.00 g) and 2M aqueous sodium carbonate solution (35.7 ml) in DMF (250 ml) was degassed. Tetrakis(triphenylphosphine)palladium(0) (2.06 g) was added under an argon atmosphere and the mixture was refluxed under heating for 21 h. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate, washed twice with water and washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and distilled under reduced pressure to give the title compound (5.84 g) as a colorless oil.

Workup

  1. customwas degassed
  2. additionTetrakis(triphenylphosphine)palladium(0) (2.06 g) was added under an argon atmosphere
  3. temperaturethe mixture was refluxed
  4. temperatureunder heating for 21 h
  5. additionWater was added to the reaction mixture
  6. extractionthe mixture was extracted with ethyl acetate
  7. washwashed twice with water
  8. washwashed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-14740fd59638486f80f8b42d9c8e9241
Source dataset
uspto-grants-2006_11
Patent number
US07141598B2

Reaction notes

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