Chloromethyl Methyl Ether → 2-nitro-5-trifluoromethylphenyl Methoxymethyl Ether

HRID 1006541Notes

Reaction equation

HRID 1006541 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[OH:14])([O-:3])=[O:2].[H-].[Na+].[CH3:17][O:18][CH2:19]Cl>CN(C=O)C>[CH3:17][O:18][CH2:19][O:14][C:5]1[CH:6]=[C:7]([C:10]([F:11])([F:12])[F:13])[CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 140916902-Nitro-5-(trifluoromethyl)phenol

Product 1

HCID 226720632-nitro-5-trifluoromethylphenyl Methoxymethyl Ether

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-nitro-5-trifluoromethylphenol (400 mg) in DMF (4.0 ml), sodium hydride (77 mg) was added at 0° C. in a stream of argon. The mixture was stirred for 30 minutes. After stirring, methoxymethyl chloride (147 μl) was added dropwise thereto. The mixture was stirred for 20 minutes. The reaction mixture was quenched by iced water and extracted with ethyl acetate. The layer containing ethyl acetate was washed, dried over and concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (hexane:AcOEt=20:1) to give the title compound (353 mg) having the following physical data.

Workup

  1. stirringAfter stirring
  2. stirringThe mixture was stirred for 20 minutes
  3. customThe reaction mixture was quenched by iced water
  4. extractionextracted with ethyl acetate
  5. additionThe layer containing ethyl acetate
  6. washwas washed
  7. customdried over and
  8. concentrationconcentrated under the reduced pressure
  9. customThe residue was purified on silica gel column chromatography (hexane:AcOEt=20:1)

Sources & evidence

ORD record
ord-1810addee9ee4cb1802e765bab944993
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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