Potassium Iodide → 9-bromo-13,13-dimethyl-6,11-diphenyl-13H-indeno[1,2-b]anthracene

HRID 40409Notes

Reaction equation

HRID 40409 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(O)[C:11]3[CH:10]=[C:9]4[C:23]5[C:28]([C:29]([CH3:31])([CH3:30])[C:8]4=[CH:7][C:6]=3[C:5]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)(O)[C:4]=2[CH:3]=1)=[CH:27][CH:26]=[CH:25][CH:24]=5.[I-].[K+].[PH2]([O-])=O.[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:6]3[CH:7]=[C:8]4[C:29]([CH3:30])([CH3:31])[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[C:9]4=[CH:10][C:11]=3[C:12]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 673867679-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diolHCID 178527019HCID 178527019, compound

Product 1

HCID 866572049-bromo-13,13-dimethyl-6,11-diphenyl-13H-indeno[1,2-b]anthraceneYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol (4.19 g, 0.0075 mol), potassium iodide (12.45 g, 0.075 mol), and sodium hypophosphite (6 g, 0.037 mol) were placed in a flask, and were suspended in acetic acid (200 ml). The reaction mixture was stirred for five hours while heating. After the reaction was terminated, the reaction solution was added to an excess of distilled water. The resultant solid was washed with distilled water, filtered, and purified by column chromatography to give 9-bromo-13,13-dimethyl-6,11-diphenyl-13H-indeno[1,2-b]anthracene (2.9 g, yield=74%).

Workup

  1. temperaturewhile heating
  2. customAfter the reaction was terminated
  3. additionthe reaction solution was added to an excess of distilled water
  4. washThe resultant solid was washed with distilled water
  5. filtrationfiltered
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-325e201e805644599f1aa2cb08829680
Source dataset
uspto-grants-2013_09
Patent number
US08525158B2

Reaction notes

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