Water → 1-Bromo-4-(methoxymethoxymethyl)benzene

HRID 457490Notes

Reaction equation

HRID 457490 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:19][O:20][CH2:21]Cl.O>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][CH2:19][O:20][CH3:21])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 701194-Bromobenzyl alcoholHCID 81531Diisopropylethylamine

Product 1

HCID 110207131-Bromo-4-(methoxymethoxymethyl)benzeneYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromobenzyl alcohol (2.8 g) and diisopropylethylamine (2.5 g) in dichloromethane (30 mL) was added chloromethyl methyl ether (1.3 g) at 0° C., and the mixture was stirred at room temperature for 14 hours. To the reaction mixture was water, and the mixture was extracted diethyl ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1) to give 1-bromo-4-[(methoxymethyloxy)methyl]benzene (3.0 g).

Workup

  1. extractionthe mixture was extracted diethyl ether
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-91e0eb6f06d24a38a775f2ac0794e823
Source dataset
uspto-grants-2007_03
Patent number
US07189702B2

Reaction notes

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