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

HRID 419414Notes

Reaction equation

HRID 419414 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[CH3:13][O:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([Cl:1])=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 225037424-Chloro-5-fluoro-2-nitrophenol

Product 1

HCID 534032891-Chloro-2-fluoro-4-methoxy-5-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-5-fluoro-2-nitrophenol (2.29 g, 12.0 mmol) was dissolved in DMF (25 mL). K2CO3 (2.5 g, 18 mmol) and iodomethane (0.893 mL, 14.3 mmol) were added and the mixture was stirred at rt overnight. The mixture was then poured into H2O and extracted with EtOAc (2×) and then the combined organics were extracted with H2O (5×). The organic layer was dried with MgSO4, filtered, and concentrated in vacuo to give the title compound of step B without further purification (2.19 g, 89%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.22 (dd, J=7.8, 1.0 Hz, 1H), 7.54 (d, J=11.4 Hz, 1H), 3.90 (d, J=1.1 Hz, 3H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. extractionthe combined organics were extracted with H2O (5×)
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53e6aceaee554e018d6d67e9b12ffe56
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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