2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 58526417, compound

HRID 2371237Notes

Reaction equation

HRID 2371237 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[CH2:6][CH2:7][CH:8]3[CH:17]([C:4]=2[CH:3]=1)[C:16]1[CH:15]=[C:14]([Br:18])[CH:13]=[CH:12][C:11]=1[CH2:10][CH2:9]3.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[CH:6]=[CH:7][C:8]3[CH:9]=[CH:10][C:11]4[CH:12]=[CH:13][C:14]([Br:18])=[CH:15][C:16]=4[C:17]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 58526348HCID 58526348, compound

Product 1

HCID 58526417HCID 58526417, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

46 g (118 mmol) of 2,11-dibromo-5,6,6a,7,8,12b-hexahydrobenzo[c]phenanthrene and 80.6 g (355 mmol) of DDQ are heated under reflux for 30 h in 300 ml of toluene. After the reaction mixture has been cooled to room temperature, the precipitated hydroquinone is filtered off and washed twice with 50 ml of toluene each time. The solvent is stripped off from the combined organic phases, and the residue is dried in vacuo. The crude product is sublimed at 190° C. and 0.01 mbar, and the sublimate is recrystallised from isopropanol. Yield: 19.6 g (110 mmol), 43%.

Workup

  1. filtrationthe precipitated hydroquinone is filtered off
  2. washwashed twice with 50 ml of toluene each time
  3. customthe residue is dried in vacuo
  4. customis sublimed at 190° C.
  5. custom0.01 mbar, and the sublimate is recrystallised from isopropanol

Sources & evidence

ORD record
ord-38ae63fc582e4328b6d7550ff30be723
Source dataset
uspto-grants-2014_04
Patent number
US08710284B2

Reaction notes

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