Dibenzofuran → 3-Nitrodibenzofuran

HRID 1022352Notes

Reaction equation

HRID 1022352 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>[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

4

Reactant 2

HCID 568DibenzofuranHCID 944Nitric Acid

Product 1

HCID 728973-NitrodibenzofuranYield 80.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

To 80 mL trifluoroacetic acid in a 250 mL round bottom flask was added dibenzofuran (7.06 g, 42 mmol) and stirred vigorously to dissolve the content at room temperature. The solution was then cooled on ice and 1.2 equivalent 70% HNO3 (4.54 g, 50.40 mmol) in 20 mL trifluoroacetic acid was poured into the stirred solution slowly. After stirring for 30 minutes contents from the flask was poured into 150 mL ice-water and stirred for another 15 minutes. Off white color precipitate was then filtered out and finally washed with 2M NaOH and water. Moist material was then recrystallized from 1.5 L boiling ethanol in the form of light yellow color crystal. 7.2 g of product was isolated.

Workup

  1. dissolutionto dissolve the content at room temperature
  2. additionwas poured into the stirred solution slowly
  3. stirringAfter stirring for 30 minutes contents from the flask
  4. stirringstirred for another 15 minutes
  5. filtrationOff white color precipitate was then filtered out
  6. washfinally washed with 2M NaOH and water
  7. customMoist material was then recrystallized from 1.5 L

Sources & evidence

ORD record
ord-df632192c9124985bb71e8f817205bc7
Source dataset
uspto-grants-2014_05
Patent number
US08722205B2

Reaction notes

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