Water → 1-Ethyl-2-fluoro-4-methoxy-5-nitrobenzene

HRID 419567Notes

Reaction equation

HRID 419567 reaction equation
[CH2:1]([C:3]1[C:8]([F:9])=[CH:7][C:6]([OH:10])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1)[CH3:2].[C:14]([O-])([O-])=O.[K+].[K+].CI.O>CS(C)=O.C(OCC)C>[CH2:1]([C:3]1[CH:4]=[C:5]([N+:11]([O-:13])=[O:12])[C:6]([O:10][CH3:14])=[CH:7][C:8]=1[F:9])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59452993HCID 59452993, compound

Product 1

HCID 594528471-Ethyl-2-fluoro-4-methoxy-5-nitrobenzeneYield 83.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

4-Ethyl-5-fluoro-2-nitrophenol (5.72 g, 30.9 mmol) was dissolved in 60 mL of DMSO with stirring. K2CO3 (6.41 g, 46.4 mmol) was added. Methyl iodide (2.5 mL, 40 mmol) was added via syringe. The reaction was stirred overnight and poured into H2O and diethyl ether. The layers were separated, and the organic layer was washed with brine. The combined aqueous layers were extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography to afford 5.13 g (83%) of the title compound of step C. 1H NMR (400 MHz, DMSO-d6) δ 7.88 (d, J=7.9 Hz, 1H), 7.23 (d, J=12.1 Hz, 1H), 3.86 (s, 3H), 2.56 (q, J=7.6 Hz, 2H), 1.11 (t, J=7.5 Hz, 3H).

Workup

  1. stirringThe reaction was stirred overnight
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. extractionThe combined aqueous layers were extracted with EtOAc (2×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-2096705a56624efe8fbc1b323e23098a
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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