Dibenzofuran → 3-Nitrodibenzofuran

HRID 1750896Notes

Reaction equation

HRID 1750896 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[N+:14]([O-])([OH:16])=[O:15]>FC(F)(F)C(O)=O.O>[N+:14]([C:3]1[CH:2]=[CH:1][C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=1)([O-:16])=[O:15]

Participants

5

Reactant 2

HCID 568Dibenzofuran2×HCID 944Nitric Acid

Product 1

HCID 728973-Nitrodibenzofuran

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

Dibenzofuran (30 g, 178 mmol) was dissolved in 276 ml, trifluoroacetic acid (TFA) and cooled in ice water bath. Fuming nitric acid 15 g (˜17 mL) was diluted with 3 mL water and then dissolved in 25 mL TFA and added to dibenzofuran solution drop wise. Reaction takes place almost instantly and a thick light green color precipitate forms. At the end of addition, flask was stirred for 20 minutes more and then poured over ice. Light green precipitate was then filtered off, washed with 2 M NaOH, dried and recrystallized from boiling ethanol 30 g (76%) of product was obtained.

Workup

  1. customReaction
  2. additionAt the end of addition, flask
  3. additionpoured over ice
  4. filtrationLight green precipitate was then filtered off
  5. washwashed with 2 M NaOH
  6. customdried
  7. customrecrystallized
  8. customwas obtained

Sources & evidence

ORD record
ord-0475104339594687ad99996c53074f38
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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