Chloromethyl Methyl Ether → HCID 58629740, compound

HRID 423260Notes

Reaction equation

HRID 423260 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([OH:12])=[C:6]([I:13])[CH:5]=1.C(N(C(C)C)CC)(C)C.[CH3:24][O:25][CH2:26]Cl>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:24][O:25][CH3:26])=[C:6]([I:13])[CH:5]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 53426739Methyl 4-hydroxy-3-iodo-5-methoxybenzoate

Product 1

HCID 58629740HCID 58629740, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-hydroxy-3-iodo-5-methoxybenzoic acid methyl ester (4.6 g) in chloroform (30 mL) were successively added diisopropylethylamine (3.88 g) and chloromethyl methyl ether (1.88 g) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. The reaction solution was washed successively with ethyl acetate, 1N hydrochloric acid, water, and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel with solvent (hexane:ethyl acetate=3:1, v/v) to give the title compound (2.70 g).

Workup

  1. temperaturecooling
  2. washThe reaction solution was washed successively with ethyl acetate, 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 with solvent (hexane

Sources & evidence

ORD record
ord-13011b04dfa34c9fbbb9408905db474d
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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