Iodine → HCID 86667149, compound

HRID 517312Notes

Reaction equation

HRID 517312 reaction equation
[Br:1][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]=[C:13]([Br:21])[CH:14]=[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>[Br:1][C:2]1[CH:3]=[C:4]2[C:23](=[CH:24][CH:25]=1)[C:7]1=[CH:8][C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][C:18]=3[CH:19]=[C:6]1[C:5]2([CH3:27])[CH3:26])[CH:15]=[CH:14][C:13]([Br:21])=[CH:12]4

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 24841Hydrogen iodideHCID 67537399HCID 67537399, compound

Product 1

HCID 86667149HCID 86667149, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,8-dibromo-13,13-dimethyl-13H-indeno[1,2-b]anthracene-6,11-dione (20 g, 0.04 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 (4.05 g, 0.016 mol) was added thereto, followed by reflux-stirring for 3 hours. After the reaction was completed, through extraction and column chromatography, 2,8-dibromo-13,13-dimethyl-13H-indeno[1,2-b]anthracene (10.9 g, yield 59%) 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-b1e31726a22243e8b9f4f2e48e1a5862
Source dataset
uspto-grants-2015_08
Patent number
US09115112B2

Reaction notes

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