4-Bromophenol → 3-(4-Hydroxyphenyl)benzonitrile

HRID 1619722ノート

反応式

HRID 1619722 の反応式
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].Br[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)=[CH:14][CH:15]=1

参加物

6

反応物 3

HCID 78084-BromophenolHCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acid

生成物 1

HCID 37790963-(4-Hydroxyphenyl)benzonitrile収率 44.4%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

3-Cyanophenylboronic acid (1.18 g, 8.03 mmol), 4-bromophenol (1.16 g, 6.69 mmol) and sodium carbonate (2.12 g, 20.07 mmol) were dissolved in dioxane (20 mL) and water (8 mL) and the reaction mixture was degassed under nitrogen. Tetrakistriphenylphosphinepalladium (0) (0.77 g, 0.67 mmol) was added and the reaction was stirred at 110° C. for 2 hours. The mixture was cooled to room temperature, filtered through pad of Arbocel™ and the filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate (30 mL) and water (15 mL). The organic layer was dried over anhydrous magnesium sulphate, filtered and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in heptane to give the title compound as a pale yellow solid (0.58 g, 44%).

後処理

  1. customwater (8 mL) and the reaction mixture was degassed under nitrogen
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through pad of Arbocel™
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was partitioned between ethyl acetate (30 mL) and water (15 mL)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in vacuo
  9. customThe residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in heptane

出典と根拠

ORDレコード
ord-eba15ac3243d4b91be0c92d5c3e6ed2c
出典データセット
uspto-grants-2014_07
特許番号
US08772293B2

反応ノート

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