Potassium Carbonate → 4'-n-Pentyl-2,5-difluoro-4-bromobiphenyl

HRID 1245268Notes

Reaction equation

HRID 1245268 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5](I)=[CH:4][C:3]=1[F:10].[CH2:11]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)[CH2:12][CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.O.C(O)C>[Br:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([C:19]2[CH:18]=[CH:17][C:16]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:21][CH:20]=2)=[C:6]([F:8])[CH:7]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 27569214-Bromo-2,5-difluoroiodobenzeneHCID 4589191(4-Pentylphenyl)boronic acid

Product 1

HCID 147660534'-n-Pentyl-2,5-difluoro-4-bromobiphenylYield 107.6%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

A mixture of 1-bromo-2,5-difluoro-4-iodbenzene (5.00 g, 15.68 mmol), 4-pentylphenylboronic acid (3.01 g, 15.67 mmol), potassium carbonate (3.25 g, 23.51 mmol), tetrabutylammonium bromide (1.26 g, 3.91 mmol), dichlorobis(triphenylphosphine)palladium (II) (0.55 g, 0.79 mmol), triphenylphosphine (0.41 g, 1.56 mmol), and a mixed solvent (toluene/water/ethanol=1/1/1, 100 ml) was refluxed for 32 hrs with stirring. The reaction mixture obtained was extracted with toluene (200 ml). The extract was washed with water (100 ml) twice and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure gave a brown oil (5.72 g). The oil was distilled under reduced pressure and was purified by silica-gel chromatography (eluent; heptane, Rf=0.58) to give a colorless oil (2.31 g).

Workup

  1. customThe reaction mixture obtained
  2. extractionwas extracted with toluene (200 ml)
  3. washThe extract was washed with water (100 ml) twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-5e3c50dce1294e3f82b86adb06034528
Source dataset
uspto-grants-2006_10
Patent number
US07125589B1

Reaction notes

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