Bromobenzene → 9-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol

HRID 40408

Reaction equation

HRID 40408 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:27]=[CH:26][C:25]2[C:24](=[O:28])[C:23]3[CH:22]=[C:21]4[C:29]5[C:34]([C:35]([CH3:37])([CH3:36])[C:20]4=[CH:19][C:18]=3[C:17](=[O:38])[C:16]=2[CH:15]=1)=[CH:33][CH:32]=[CH:31][CH:30]=5.[CH2:39]1COC[CH2:40]1>>[Br:13][C:14]1[CH:27]=[CH:26][C:25]2[C:24]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)([OH:28])[C:23]3[CH:22]=[C:21]4[C:29]5[C:34]([C:35]([CH3:36])([CH3:37])[C:20]4=[CH:19][C:18]=3[C:17]([C:9]3[CH:40]=[CH:39][CH:12]=[CH:11][CH:10]=3)([OH:38])[C:16]=2[CH:15]=1)=[CH:33][CH:32]=[CH:31][CH:30]=5

Participants

5

Reactant 4

HCID 7961BromobenzeneHCID 8028TetrahydrofuranHCID 581752939-bromo-13,13-dimethyl-6H-indeno[1,2-b]anthracene-6,11(13H)-dioneHCID 178418339Butyllithium

Product 1

HCID 673867679-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diolYield 63%

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 −780, and the reaction mixture was stirred for one hour at a maintained temperature. Then, 9-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 12 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 9-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol (8.5 g, yield=63%).

Workup

  1. additionwas gradually added at −780
  2. stirringthe reaction mixture was stirred at room temperature for 12 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-14aad029301941c69d94abba4b869465
Source dataset
uspto-grants-2013_09
Patent number
US08525158B2

Linked notes

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