Methyl iodide → 5-Methoxy-2-nitrobenzotrifluoride

HRID 2308241Notes

Reaction equation

HRID 2308241 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12])([O-:3])=[O:2].[C:15]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O.C1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:15])=[CH:6][C:5]=1[C:11]([F:12])([F:13])[F:14])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 69314-Nitro-3-trifluoromethylphenolHCID 11430Potassium Carbonate

Product 1

HCID 5485175-Methoxy-2-nitrobenzotrifluorideYield 94%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 241BenzeneSolvent

Procedure

A solution of 4-nitro-3-trifluoromethylphenol (27 g, 130 mmol) in acetone (250 mL) was treated with K2CO3 (18 g, 130 mmol) and methyl iodide (16 mL, 260 mmol) and the mixture was heated at reflux under nitrogen. After 16 h, the cooled mixture was filtered to remove K2CO3 and the filtrate was concentrated in vacuo to give the crude product (32 g), which was taken up in benzene (250 mL). The organic solution was washed with water and brine (125 mL each), dried (MgSO4) and concentrated in vacuo to give the title compound (27 g, 94%) as a yellow oil which was pure enough for further use.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux under nitrogen
  3. filtrationthe cooled mixture was filtered
  4. customto remove K2CO3
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give the crude product (32 g), which
  7. washThe organic solution was washed with water and brine (125 mL each)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb03fcf919484da0bfc98b616ae344e2
Source dataset
uspto-grants-2004_12
Patent number
US06835745B2

Reaction notes

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