Chloromethyl Methyl Ether → 4-Bromo-2-(2-methoxymethoxyethyl)-anisole

HRID 264917

Reaktionsgleichung

Reaktionsgleichung von HRID 264917
C(N(C(C)C)C(C)C)C.[CH3:10][O:11][CH2:12]Cl.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([CH2:23][CH2:24][OH:25])[CH:16]=1.[OH-].[NH4+]>ClCCl.O>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([CH2:23][CH2:24][O:25][CH2:10][O:11][CH3:12])[CH:16]=1

Komponenten

7

Edukt 4

HCID 7864Chloromethyl Methyl EtherHCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 15020172-(5-Bromo-2-methoxyphenyl)ethan-1-ol

Produkt 1

HCID 214585954-Bromo-2-(2-methoxymethoxyethyl)-anisole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.48 g of N-ethyl-diisopropylamine and 0.49 g of chlorodimethyl ether are added at room temperature to a solution of 948 mg of 4-bromo-2-(2-hydroxyethyl)-anisole in 30 ml of dichloromethane. The reaction mixture is stirred for 200 minutes at room temperature, and then 1 ml of water and 1 ml of 25% ammonium hydroxide solution are added thereto. The two-phase mixture is stirred vigorously for a further 15 minutes and then the organic phase is separated off, dried over sodium sulfate and concentrated by evaporation. Purification of the residue by means of FC (hexane/dichloromethane=1:1) yields the title compound: Rf (dichloromethane)=0.6; HPLC Rt =17.33 minutes.

Aufarbeitung

  1. stirringThe two-phase mixture is stirred vigorously for a further 15 minutes
  2. customthe organic phase is separated off
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customPurification of the residue by means of FC (hexane/dichloromethane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-5418a447fbbc44fdaa404f13762049d5
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646143

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