Potassium Iodide → 9-bromo-13,13-dimethyl-6,11-di(naphthalen-2-yl)-13H-indeno[1,2-b]anthracene

HRID 40410Notes

Reaction equation

HRID 40410 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]([C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=3)(O)[C:11]3[CH:10]=[C:9]4[C:27]5[C:32]([C:33]([CH3:35])([CH3:34])[C:8]4=[CH:7][C:6]=3[C:5]([C:37]3[CH:46]=[CH:45][C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=3)(O)[C:4]=2[CH:3]=1)=[CH:31][CH:30]=[CH:29][CH:28]=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:37]3[CH:46]=[CH:45][C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=3)[C:6]3[CH:7]=[C:8]4[C:33]([CH3:35])([CH3:34])[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[C:9]4=[CH:10][C:11]=3[C:12]=2[C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 581753369-bromo-13,13-dimethyl-6,11-di(naphthalen-2-yl)-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diolHCID 178527019HCID 178527019, compound

Product 1

HCID 581752899-bromo-13,13-dimethyl-6,11-di(naphthalen-2-yl)-13H-indeno[1,2-b]anthraceneYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9-bromo-13,13-dimethyl-6,11-di(naphthalen-2-yl)-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol (11.87 g, 0.018 mol), Potassium iodide (29.88 g, 0.18 mol), and Sodium hypophosphite (35.63 g, 0.297 mol) were placed in a flask, and were suspended in acetic acid (300 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, filtered and purified by column chromatography to give 9-bromo-13,13-dimethyl-6,11-di(naphthalen-2-yl)-13H-indeno[1,2-b]anthracene (8 g, yield=71%).

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
  5. filtrationfiltered
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-f685fddc85a44e5698379e61393ca7bf
Source dataset
uspto-grants-2013_09
Patent number
US08525158B2

Reaction notes

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