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Chloroform → 7-Bromo-9-(1,1-ethylenedioxy)ethyl-6,9-dihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

HRID 64904
Notes
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Reaction equation

HRID 64904 reaction equation
[CH2:1]1[CH2:28][O:27][C:3]2([C:20]3[C:19](=[O:21])[C:18]4[C:9](=[C:10]([OH:23])[C:11]5[CH2:12][CH2:13][CH:14]([OH:22])[CH2:15][C:16]=5[CH:17]=4)[C:8](=[O:24])[C:7]=3[CH:6]=[CH:5][CH:4]2[CH2:25][CH3:26])[O:2]1.C(Cl)(Cl)Cl.[Br:33]Br.N(C(C)(C)C#N)=NC(C)(C)C#N>O.C(Cl)(Cl)(Cl)Cl>[Br:33][CH:12]1[CH2:13][CH:14]([OH:22])[CH2:15][C:16]2[CH:17]=[C:18]3[C:9]([C:8](=[O:24])[C:7]4[CH:6]=[CH:5][CH:4]([CH2:25][CH3:26])[C:3]5([O:2][CH2:1][CH2:28][O:27]5)[C:20]=4[C:19]3=[O:21])=[C:10]([OH:23])[C:11]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6547AzobisisobutyronitrileHCID 24408BromineHCID 131714853HCID 131714853, compound

Product 1

HCID 867409987-Bromo-9-(1,1-ethylenedioxy)ethyl-6,9-dihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dioneYield 72.7%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 9-(1,1-ethylenedioxy)ethyl-6,9-dihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione (657 mg), chloroform (33 ml), carbon tetrachloride (13 ml) and water (26 ml) was stirred at room temperature, and bromine (530 mg) and azobisisobutyronitrile (130 mg) were added thereto, and the resulting mixture was stirred at the same temperature as above for 1 hour. From the reaction mixture, the organic phase was separated, washed with water, dried over anhydrous sodium sulfate and concentrated. The residue was crystallized from ether to give 7-bromo-9-(1,1-ethylenedioxy)ethyl-6,9-dihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione (576 mg). M.P., 173°-176° C.

Workup

  1. stirringthe resulting mixture was stirred at the same temperature as above for 1 hour
  2. customFrom the reaction mixture, the organic phase was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-8ecf2cf6f97e40be8c3c26a4108732d5
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04610986

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes