Iodine → HCID 59742048, compound

HRID 517306Notes

Reaction equation

HRID 517306 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:23](=[CH:24][CH:25]=1)[C:7]1=[CH:8][C:9]3[C:10](=O)[C:11]4[CH:12]=[CH:13][C:14](Br)=[CH:15][C:16]=4[C:17](=O)[C:18]=3[CH:19]=[C:6]1[C:5]2([CH3:27])[CH3:26].I.O.II>C(O)(=O)C>[CH3:26][C:5]1([CH3:27])[C:6]2[C:7](=[CH:8][C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][C:18]=3[CH:19]=2)[CH:15]=[CH:14][CH:13]=[CH:12]4)[C:23]2[C:4]1=[CH:3][CH:2]=[CH:25][CH:24]=2

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 24841Hydrogen iodideHCID 58175328HCID 58175328, compound

Product 1

HCID 59742048HCID 59742048, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,9-dibromo-13,13-dimethyl-6H-indeno[1,2-b]anthracene-6,11(13H)-dione (19 g, 0.058 mol) was dissolved in acetic acid (200 ml), and added with 57% HI (50 ml), followed by reflux-stirring for 48 hours. After the reaction was completed, the resultant solution was added with distilled water (500 ml). The produced solid was filtered and dissolved in toluene (200 ml) and iodine (4.56 g, 0.018 mol) was added thereto, followed by reflux-stirring for 3 hours. After the reaction was completed, through extraction and column chromatography, 13,13-dimethyl-13H-indeno[1,2-b]anthracene (10 g, yield 54%) was obtained.

Workup

  1. filtrationThe produced solid was filtered
  2. dissolutiondissolved in toluene (200 ml)
  3. stirringby reflux-stirring for 3 hours
  4. extractionAfter the reaction was completed, through extraction and column chromatography

Sources & evidence

ORD record
ord-951760f5b90d4b86a297575b23a59264
Source dataset
uspto-grants-2015_08
Patent number
US09115112B2

Reaction notes

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