Dimethyl Sulfoxide → Methyl 4-fluoro-2-(6-nitropyridin-3-yloxy)benzoate

HRID 573101Notes

Reaction equation

HRID 573101 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.Cl[C:14]1[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[N:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([F:1])=[CH:3][C:4]=1[O:12][C:14]1[CH:19]=[N:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 2598065-Chloro-2-nitropyridineHCID 2775386Methyl 4-fluorosalicylate

Product 1

HCID 67226297Methyl 4-fluoro-2-(6-nitropyridin-3-yloxy)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Methyl 4-fluoro-2-hydroxybenzoate (3.00 g), 5-chloro-2-nitropyridine (3.08 g), and potassium carbonate (4.87 g) were added to dimethyl sulfoxide (50 mL), heated to 110° C. for one hour, cooled, added to water, and extracted with ethyl ether. The ether was washed with brine and dried on anhydrous sodium sulfate. The solution was filtered and concentrated and purified by flash column chromatography on silica gel using 10% ethyl acetate in hexanes increasing to 20% ethyl acetate in hexanes and increasing again to 30% ethyl acetate in hexanes.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl ether
  3. washThe ether was washed with brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography on silica gel using 10% ethyl acetate in hexanes increasing to 20% ethyl acetate in hexanes
  8. temperatureincreasing again to 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3e1e66c9771147c3a785f10b0144ee9e
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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