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

HRID 1470905Notes

Reaction equation

HRID 1470905 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-a5b8f75621644e258840b2293a78cba2
Source dataset
uspto-grants-2015_04
Patent number
US09006503B2

Reaction notes

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