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

HRID 40411Notes

Reaction equation

HRID 40411 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][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[C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH:40]=[CH:39][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[C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH:40]=[CH:39][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[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 673868939-bromo-13,13-dimethyl-6,11-di(naphthalen-1-yl)-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diolHCID 178527019HCID 178527019, compound

Product 1

HCID 866572059-bromo-13,13-dimethyl-6,11-di(naphthalen-1-yl)-13H-indeno[1,2-b]anthraceneYield 57.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9-bromo-13,13-dimethyl-6,11-di(naphthalen-1-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 with distilled water, filtered, and purified by column chromatography to give 9-bromo-13,13-dimethyl-6,11-di(naphthalen-1-yl)-13H-indeno[1,2-b]anthracene (6.5 g, yield=57%)

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-eef15c4ab9f1421a86cd6e960b227d5f
Source dataset
uspto-grants-2013_09
Patent number
US08525158B2

Reaction notes

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