4-Iodophenol → 4-(3-Trifluoromethylphenyl)phenol

HRID 1619621ノート

反応式

HRID 1619621 の反応式
C(=O)([O-])O.[Na+].[F:6][C:7]([F:18])([F:17])[C:8]1[CH:9]=[C:10](B(O)O)[CH:11]=[CH:12][CH:13]=1.I[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1>O1CCOCC1.Cl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:6][C:7]([F:18])([F:17])[C:8]1[CH:9]=[C:10]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[CH:11]=[CH:12][CH:13]=1

参加物

7

反応物 3

HCID 108944-IodophenolHCID 516892Sodium BicarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acid

生成物 1

HCID 200995974-(3-Trifluoromethylphenyl)phenol収率 30.4%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

An aqueous solution of sodium hydrogen carbonate (6.9 g in 18 mL water, 82 mmol) was added to a stirred solution of 3-trifluoromethylbenzeneboronic acid (7.77 g, 41 mmol) and 4-iodophenol (6.0 g, 30 mmol) in 1,4-dioxane (90 mL). The reaction mixture was degassed, then tetrakis(triphenylphosphine) palladium (0) (1.58 g, 1.36 mmol) was added and the reaction mixture heated at 100° C. for 18 hours. The mixture was diluted with a 2M aqueous solution of HCl and extracted with ethyl acetate (50 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (5%-40% ethyl acetate in heptane gradient elution) to afford the title compound (2.17 g, 30%) as an oil.

後処理

  1. customThe reaction mixture was degassed
  2. extractionextracted with ethyl acetate (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (5%-40% ethyl acetate in heptane gradient elution)

出典と根拠

ORDレコード
ord-0f79d83225b7446186e4194d4f1a7b87
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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