Sodium borohydride → 2,9-dibromo-13,13-dimethyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol

HRID 1945364Notes

Reaction equation

HRID 1945364 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:23](=[CH:24][CH:25]=1)[C:7]1=[CH:8][C:9]3[C:10](=[O:22])[C:11]4[CH:12]=[CH:13][C:14]([Br:21])=[CH:15][C:16]=4[C:17](=[O:20])[C:18]=3[CH:19]=[C:6]1[C:5]2([CH3:27])[CH3:26].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:23](=[CH:24][CH:25]=1)[C:7]1=[CH:8][C:9]3[CH:10]([OH:22])[C:11]4[CH:12]=[CH:13][C:14]([Br:21])=[CH:15][C:16]=4[CH:17]([OH:20])[C:18]=3[CH:19]=[C:6]1[C:5]2([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58175328HCID 58175328, compound

Product 1

HCID 581754702,9-dibromo-13,13-dimethyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diolYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,9-Dibromo-13,13-dimethyl-6H-indeno[1,2-b]anthracene-6,11(13H)-dione (20 g, 1 eq, 0.041 mol) was placed in a flask, and MeOH (150 ml) was added thereto. Then, sodium borohydride (6.2 g, 4 eq, 0.164 mol) was gradually added at 0° C., the reaction mixture was stirred for five hours, and ice water was gradually added thereto. The reaction solution was extracted with MC and recrystallized from hexane to give 2,9-dibromo-13,13-dimethyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol (15 g, yield=78%).

Workup

  1. extractionThe reaction solution was extracted with MC
  2. customrecrystallized from hexane

Sources & evidence

ORD record
ord-ac59e50d87c04a9d978da266c3fb4f89
Source dataset
uspto-grants-2013_03
Patent number
US08395144B2

Reaction notes

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