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

HRID 1619621노트

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HRID 1619621 반응식
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

참가 물질

7

반응물 3

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

생성물 1

HCID 200995974-(3-Trifluoromethylphenyl)phenol수율 30.4%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0f79d83225b7446186e4194d4f1a7b87
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772293B2

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