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

HRID 744805

Reaction equation

HRID 744805 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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)=0.5; HPLC Rt =17.33 minutes.

Workup

  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)

Sources & evidence

ORD record
ord-b6657108f1f84ae7ad051748ab354c80
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Linked notes

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