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

HRID 1247728Notes

Reaction equation

HRID 1247728 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-614deb62bd5d4988b30a80d8d63c5b81
Source dataset
uspto-grants-2006_10
Patent number
US07129381B2

Reaction notes

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