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

HRID 1245268노트

반응식

HRID 1245268 반응식
[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

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 74236Tetrabutylammonium Bromide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 86587398Ethanol toluene water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5e3c50dce1294e3f82b86adb06034528
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07125589B1

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