Tris(1,1-dimethylethyl)phosphine → 2-(4'-Vinyl-biphenyl-4-yl)pyridine

HRID 1639944

反応式

HRID 1639944 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[CH2:2].Cl[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:15][CH:14]=1.F[K].C(P)(C)(C)C.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd].O1CCOCC1>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:17][CH:18]=2)=[CH:5][CH:4]=1)=[CH2:2]

参加物

8

反応物 5

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 123165tert-ButylphosphineHCID 27343934-Vinylphenylboronic acidHCID 27578492-(4-Chlorophenyl)pyridineHCID 178506427HCID 178506427、化合物

生成物 1

HCID 667224942-(4'-Vinyl-biphenyl-4-yl)pyridine収率 45%

試薬・触媒・溶媒 2

HCID 44556509Tris(dibenzylideneacetone) palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

Under a nitrogen stream, 23.42 g (0.158 mol) of 4-vinyl-phenyl boronic acid, 20.0 g (0.1055 mol) of 2-(4-chloro-phenyl)pyridine, 500□ of 1,4-dioxane, 27.54 g (0.474 mol, 3.3 equivalent) of fluoro-potassium, 1.69 g (0.0084 mol, 5.3 mol %) of t-butylphosphine [P(t-Bu)3)], and 2.6 g (0.0028 mol, 1.8 mol %) of palladium tris(dibenzylidene acetone) [Pd2(dba)3] were placed into a 2-neck round flask 250□. After the resulting solution was heated to reflux at 80° C. for 24 hours, the reaction was terminated. The resulting mixture was filtered, the catalyst and fluoro-potassium that were black solids were removed, and then the dioxane was removed by rotary evaporation. After extraction with 300□ of dichloromethane and 400□ of distilled water, the residue was subjected to column chromatography using a mixed solution of hexane and ethylacetate (7:3) as a developing solvent and then recrystallized at 0° C. using ethylacetate to give the 2-(4′-vinyl-biphenyl-4-yl)pyridine. The yield was 45%. As the structural characteristics of the thus prepared 2-(4′-vinyl-biphenyl-4-yl)pyridine, the 1H-NMR spectrum is shown in FIG. 2, the UV/Vis is shown in FIG. 3, the GC-Mass is shown in FIG. 4, and the FT-IR is shown in FIG. 5. Moreover, the analysis data of the 2-(4′-vinyl-biphenyl-4-yl)pyridine is shown in the following table 1:

後処理

  1. temperatureAfter the resulting solution was heated
  2. customthe reaction was terminated
  3. filtrationThe resulting mixture was filtered
  4. customwere removed
  5. customthe dioxane was removed by rotary evaporation
  6. extractionAfter extraction with 300□ of dichloromethane and 400□ of distilled water
  7. customrecrystallized at 0° C.

出典と根拠

ORDレコード
ord-1455a27782084f089190e0cebd8c079e
出典データセット
uspto-grants-2012_02
特許番号
US08110642B2

関連ノート

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