Styrene → 5-Chloro-2-methoxy-beta-phenylstyrene

HRID 644447

Reaktionsgleichung

Reaktionsgleichung von HRID 644447
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[CH2:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH3:10])=[C:2]([CH:7]=1)[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 7501StyreneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 5219352-Bromo-4-chloroanisole

Produkt 1

HCID 685787655-Chloro-2-methoxy-beta-phenylstyreneAusbeute 35,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Palladium acetate (21 mg, 7 mol %) was added to a solution of 2-bromo-4-chloroanisole (300 mg, 1.4 mmol), styrene (211 mg, 2 mmol), triethylamine (13 μL, 0.1 mmol) and triphenylphosphine (50 mg, 1.9 mmol) in acetonitrile (6 mL), and the mixture was refluxed for 8 hours under argon atmosphere. After the reaction mixture was cooled to room temperature, the solvent was concentrated under reduced pressure and the obtained residue was diluted with ethyl acetate (15 mL). After the solution was washed successively with 2N hydrochloric acid, water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1) to give the title compound (118 mg, 35.6%) as a white powder.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 8 hours under argon atmosphere
  2. concentrationthe solvent was concentrated under reduced pressure
  3. additionthe obtained residue was diluted with ethyl acetate (15 mL)
  4. washAfter the solution was washed successively with 2N hydrochloric acid, water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe residue obtained by evaporation of the solvent under reduced pressure
  7. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-bc323d90db4149c59ce4603da76843ae
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700655B2

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