Methyl iodide → 4-Bromo-4'-methoxymethylbiphenyl

HRID 1626823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626823
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:16]I.[H-].[Na+].[Cl-].[NH4+]>O1CCCC1>[CH3:16][O:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1393673[4-(4-Bromophenyl)phenyl]methanol

Produkt 1

HCID 681932604-Bromo-4'-methoxymethylbiphenylAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(4′-Bromobiphenyl-4-yl)methanol (1.2 g, 4.6 mmol) was dissolved in tetrahydrofuran (20 mL), and methyl iodide (0.97 g, 6.8 mmol), and then sodium hydride (63%, 0.26 g, 6.8 mmol) were added under a nitrogen atmosphere at 4° C., followed by stirring at room temperature for 30 minutes. A saturated aqueous ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/dichloromethane), and a fraction corresponding to the Rf value=0.50 (hexane/dichloromethane=1/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (1.2 g, 4.3 mmol) as a white solid (yield 95%).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/dichloromethane)
  4. concentrationa fraction corresponding to the Rf value=0.50 (hexane/dichloromethane=1/1) by thin layer chromatography was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5073859ddfc64a1e9600d1629e571b80
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785462B2

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