Water → 2-Fluoro-4-(methoxymethoxy)-1-nitrobenzene

HRID 1042105Notes

Reaction equation

HRID 1042105 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[H-].[Na+].[CH3:14][O:15][CH2:16]Cl.O>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([O:11][CH2:14][O:15][CH3:16])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 199324002-Fluoro-4-(methoxymethoxy)-1-nitrobenzeneYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-fluoro-4-nitrophenol (120 g) in N,N-dimethylformamide (500 mL) was added sodium hydride (oily, 60%) (22 g) under ice-cooling, and the mixture was stirred for 30 min. To the reaction solution was added chloromethyl methyl ether (64 mL) and the mixture was stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was subjected to basic column chromatography (ethyl acetate) to give the title compound (98 g, yield 64%) as a yellow oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained crude product

Sources & evidence

ORD record
ord-0acfc9fed64f441f8934e1386ebb9c06
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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