Nitric Acid → HCID 67355479, compound

HRID 2272276Notes

Reaction equation

HRID 2272276 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:18][C:11]=3[C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1.[N+:26]([O-])([OH:28])=[O:27]>C(Cl)(Cl)Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:21]=[C:20]([N+:26]([O-:28])=[O:27])[C:19]([O:22][CH:23]([CH3:24])[CH3:25])=[CH:18][C:11]=3[C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 67354738HCID 67354738, compound2×

Product 1

HCID 67355479HCID 67355479, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethyl 2-(4-chlorophenyl)-5-isopropoxybenzofuran-3-carboxylate 4 (30 g, 0.084 mol) was dissolved in chloroform (75 mL) and the resulting solution was cooled in an ice bath. Nitric acid (55 mL) was also dissolved in chloroform (75 mL) and cooled in an ice bath. The acid solution was added dropwise to the solution of ethyl 2-(4-chlorophenyl)-5-isopropoxybenzofuran-3-carboxylate over 1 hour, and the reaction mixture was then stirred at 0° C. for 1.5 hrs. The reaction mixture was then diluted with water (60 mL) and the layers were separated. The organic layer was dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give a brown oil which was purified by column chromatography (5/1 PE/EA) to afford ethyl 2-(4-chlorophenyl)-5-isopropoxy-6-nitrobenzofuran-3-carboxylate as a brown solid (11 g, 32%).

Workup

  1. temperaturethe resulting solution was cooled in an ice bath
  2. temperaturecooled in an ice bath
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a brown oil which
  8. customwas purified by column chromatography (5/1 PE/EA)

Sources & evidence

ORD record
ord-7d566a8461784e73bfd65c95d8729a77
Source dataset
uspto-grants-2015_09
Patent number
US09119868B2

Reaction notes

Loading…