2-Bromo-13,13-dimethyl-6,11-di(naphthalen-2-yl)-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol → 2-Bromo-13,13-dimethyl-6,11-di(naphthalen-2-yl)-13h-indeno[1,2-b]anthracene

HRID 40406Notes

Reaction equation

HRID 40406 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:42](=[CH:43][CH:44]=1)[C:7]1=[CH:8][C:9]3[C:10]([C:32]4[CH:41]=[CH:40][C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[CH:33]=4)(O)[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=4[C:17]([C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH:22]=4)(O)[C:18]=3[CH:19]=[C:6]1[C:5]2([CH3:46])[CH3:45].[PH2]([O-])=O.[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:42](=[CH:43][CH:44]=1)[C:7]1=[CH:8][C:9]3[C:10]([C:32]4[CH:41]=[CH:40][C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[CH:33]=4)=[C:11]4[C:16](=[C:17]([C:21]5[CH:30]=[CH:29][C:28]6[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=6)[CH:22]=5)[C:18]=3[CH:19]=[C:6]1[C:5]2([CH3:46])[CH3:45])[CH:15]=[CH:14][CH:13]=[CH:12]4

Participants

4

Reactant 2

HCID 581754872-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 581755502-Bromo-13,13-dimethyl-6,11-di(naphthalen-2-yl)-13h-indeno[1,2-b]anthraceneYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-bromo-13,13-dimethyl-6,11-di(naphthalen-2-yl)-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol (5 g, 0.0075 mol), KI (12.45 g, 0.075 mol), and Sodium hypophosphite (6 g, 0.037 mol) were placed in a flask, and acetic acid (200 ml) was added thereto. 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 2-bromo-13,13-dimethyl-6,11-di(naphthalen-2-yl)-13H-indeno[1,2-b]anthracene (3.56 g, yield=76%).

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-20caf7a413a84dcaa1170aaff5e338f4
Source dataset
uspto-grants-2013_09
Patent number
US08525158B2

Reaction notes

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