Water → 1-Bromo-4-[2-(methoxymethoxy)ethyl]benzene

HRID 1826634Notes

Reaction equation

HRID 1826634 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:20][O:21][CH2:22]Cl.O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:20][O:21][CH3:22])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 728512-(4-Bromophenyl)ethanolHCID 81531Diisopropylethylamine

Product 1

HCID 155094031-Bromo-4-[2-(methoxymethoxy)ethyl]benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-bromophenyl)ethanol (1.0 g) and diisopropylethylamine (1.3 mL) in dichloromethane (5 mL) was added chloromethyl methyl ether (0.75 mL), and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added water, and the organic layer was separated and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=15/1–10/1) to give 1-bromo-4-[2-(methoxymethyloxy)ethyl]-benzene (1.2 g).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=15/1–10/1)

Sources & evidence

ORD record
ord-737d707b27724810a3101c1403445733
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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