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

HRID 1945361Notes

Reaction equation

HRID 1945361 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].[I-].[K+].[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

5

Reactant 3

HCID 4875Potassium IodideHCID 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, 1 eq, 0.0075 mol), potassium iodide (12.45 g, 10 eq, 0.075 mol), and sodium hypophosphite (6 g, 5 eq, 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, filtered, and purified by column chromatography to give a target compound (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
  5. filtrationfiltered
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-75e49b012ecd4ca48f50631dd1b7437e
Source dataset
uspto-grants-2013_03
Patent number
US08395144B2

Reaction notes

Loading…