Chloromethyl Methyl Ether → 5-Bromo-4-methoxymethoxyisophthalic acid dimethyl ester

HRID 423266Notes

Reaction equation

HRID 423266 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:13]=[C:12]([Br:14])[C:11]([OH:15])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.C(N(C(C)C)CC)(C)C.[CH3:26][O:27][CH2:28]Cl>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:13]=[C:12]([Br:14])[C:11]([O:15][CH2:26][O:27][CH3:28])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 58629779Dimethyl 5-bromo-4-hydroxybenzene-1,3-dicarboxylate

Product 1

HCID 666771415-Bromo-4-methoxymethoxyisophthalic acid dimethyl esterYield 60.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-bromo-4-hydroxyisophthalic acid dimethyl ester (12.3 g) in chloroform (130 mL) were successively added diisopropylethylamine (8.24 g) and methoxymethyl chloride (4.11 g) under ice-cooling, and the mixture was stirred at room temperature overnight. The reaction solution was washed successively with 1N hydrochloric acid, water, and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1, v/v) to give the title compound (8.52 g).

Workup

  1. temperaturecooling
  2. washThe reaction solution was washed successively with 1N hydrochloric acid, water, and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-adf942f4176f422fb900a8b4a741bfab
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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