Trifluoroacetic acid → 2-iodophenanthrene-9,10-dione

HRID 2195576Notes

Reaction equation

HRID 2195576 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.[I:24]N1C(=O)CCC1=O>O>[I:24][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12](=[O:16])[C:13](=[O:15])[C:14]=2[CH:1]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 67639,10-PhenanthrenedioneHCID 120273N-Iodosuccinimide

Product 1

HCID 3517612-iodophenanthrene-9,10-dioneYield 75.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

Into a 200 mL volume eggplant-shaped flask, 10.0 g of 9,10-phenanthrenequinone, 54.8 g of trifluoroacetic acid, and 21.6 g of N-iodosuccinimide were added at room temperature, heated to 35° C., and then stirred for 36 hours in an argon atmosphere. The reaction mixture was poured into icy water. The solid precipitate was collected by filtration and recrystallized with tetrahydrofuran, thereby to give 12.1 g of 2-iodo-phenantrene-9,10-dione (yield 75%) as an orange-colored solid.

Workup

  1. filtrationThe solid precipitate was collected by filtration
  2. customrecrystallized with tetrahydrofuran

Sources & evidence

ORD record
ord-b5375db1cc9e4047998db26732dcdee8
Source dataset
uspto-grants-2012_12
Patent number
US08338027B2

Reaction notes

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