Bromobenzene → 2-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol

HRID 40404Notes

Reaction equation

HRID 40404 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li][CH2:9][CH2:10][CH2:11][CH3:12].[Br:13][C:14]1[CH:15]=[C:16]2[C:34](=[CH:35][CH:36]=1)[C:19]1=[CH:20][C:21]3[C:22](=[O:33])[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[C:29](=[O:32])[C:30]=3[CH:31]=[C:18]1[C:17]2([CH3:38])[CH3:37].[CH2:39]1COC[CH2:40]1>>[Br:13][C:14]1[CH:15]=[C:16]2[C:34](=[CH:35][CH:36]=1)[C:19]1=[CH:20][C:21]3[C:22]([C:9]4[CH:40]=[CH:39][CH:12]=[CH:11][CH:10]=4)([OH:33])[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[C:29]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)([OH:32])[C:30]=3[CH:31]=[C:18]1[C:17]2([CH3:38])[CH3:37]

Participants

5

Reactant 4

HCID 7961BromobenzeneHCID 8028TetrahydrofuranHCID 581753612-Bromo-13,13-dimethyl-6H-indeno(1,2-b)anthracene-6,11(13H)-dioneHCID 178418339Butyllithium

Product 1

HCID 673870832-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diolYield 82%

Procedure

Bromobenzene (8.5 g, 0.054 mol) was placed in a flask, and THF (200 ml) was added thereto. After dissolution, n-BuLi (38.4 ml, 0.06 mol) was gradually added at −78□, and the reaction mixture was stirred for one hour at a maintained temperature. Then, 2-bromo-13,13-dimethyl-6H-indeno[1,2-b]anthracene-6,11(13H)-dione (10 g, 0.024 mol) was added and the reaction mixture was stirred at room temperature for 17 hours. After the reaction was terminated, the reaction solution was washed with distilled water, extracted with ethyl acetate, and purified by column chromatography to give 2-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol (11 g, yield=82%).

Workup

  1. additionwas gradually added at −78□, and the reaction mixture
  2. stirringthe reaction mixture was stirred at room temperature for 17 hours
  3. customAfter the reaction was terminated
  4. washthe reaction solution was washed with distilled water
  5. extractionextracted with ethyl acetate
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-c075f70a111f43b0b457dcd343c71a4b
Source dataset
uspto-grants-2013_09
Patent number
US08525158B2

Reaction notes

Loading…