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

HRID 1245268ノート

反応式

HRID 1245268 の反応式
[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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 74236Tetrabutylammonium Bromide触媒HCID 178418476HCID 178418476、化合物触媒HCID 86587398Ethanol toluene water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5e3c50dce1294e3f82b86adb06034528
出典データセット
uspto-grants-2006_10
特許番号
US07125589B1

反応ノート

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