Dimethylformamide → 1-Iodo-2-(methoxymethoxy)benzene

HRID 1359281Notes

Reaction equation

HRID 1359281 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].CN(C)C=O.[CH3:16][O:17][CH2:18]Cl>C(OCC)(=O)C.O>[CH3:16][O:17][CH2:18][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[I:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 107842-IodophenolHCID 24758Sodium hydride

Product 1

HCID 117474651-Iodo-2-(methoxymethoxy)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

216 mg of 60% oily sodium hydride was added to a mixture of 1.65 of 2-iodophenol and 20 ml of N,N-dimethylformamide under ice-cooling followed by stirring at room temperature for 30 minutes. Under ice-cooling, 570 μl of chloromethyl methyl ether was added thereto, followed by stirring for 30 minutes at room temperature. Water and ethyl acetate were added thereto. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed, to give 2.12 g of the target compound.

Workup

  1. temperaturecooling
  2. temperatureUnder ice-cooling
  3. stirringby stirring for 30 minutes at room temperature
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-b0de47e6053a41e7aedc433c8c62a127
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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