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

HRID 1982832Notes

Reaction equation

HRID 1982832 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.Cl[CH2:21][O:22][CH3:23].O>ClCCl>[CH3:21][O:22][CH2:23][O:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=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 chloromethylmethyl 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, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=15/1-10/1) to give 4-[2-(methoxymethyloxy)ethyl]bromobenzene (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-b24351e709ad4284a65fc6a71b6a6f01
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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