Methyl iodide → 2-Methoxy-1-nitro-3-(trifluoromethyl)benzene

HRID 751068Notes

Reaction equation

HRID 751068 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:5]=1[OH:14])([O-:3])=[O:2].[C:15]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[C:5]=1[O:14][CH3:15])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 9018342-Nitro-6-(trifluoromethyl)phenol

Product 1

HCID 219358692-Methoxy-1-nitro-3-(trifluoromethyl)benzeneYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of compound 17A (1.4 g, 6.76 mmol) and K2CO3 (1.4 g, 10 mmol) in DMF (60 mL) was added iodomethane (0.46 mL, 7.44 mmol). After the addition, the mixture was stirred at 40° C. overnight, then cooled to rt, partitioned between ether and water. The separated ether layer was washed with water and brine, then dried (Na2SO4) and concentrated under reduced pressure. The residue was chromatographed (silica gel) eluting with 10% EtOAc/hexane to yield the title compound (1.38 g, 92% yield).

Workup

  1. additionAfter the addition
  2. temperaturecooled to rt
  3. custompartitioned between ether and water
  4. washThe separated ether layer was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed (silica gel)
  8. washeluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-f9e0cae2a3f641c3a666d31cb8c286c3
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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