2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 68726109, compound

HRID 1892066Notes

Reaction equation

HRID 1892066 reaction equation
[Br:1][C:2]1[CH2:3][CH2:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][C:6]=2[CH3:14].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5](=[CH:4][CH:3]=1)[C:6]([CH3:14])=[CH:7][C:8]([O:12][CH3:13])=[CH:9]2

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 68728221HCID 68728221, compound

Product 1

HCID 68726109HCID 68726109, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the solution of 3-bromo-6-methoxy-8-methyl-1,2-dihydro-naphthalene (8.0 g, 0.03 mol) from Step 3 in 1,4-dioxane (40 ml), DDQ (7.9 g, 0.03 mol) was added and the mixture was refluxed for 2 h. The solvent was removed and the crude product was purified by chromatography (silica gel:hexane:ethyl acetate/20:1) to provide 6-bromo-3-methoxy-1-methyl-naphthalene, 3.7 g.

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customThe solvent was removed
  3. customthe crude product was purified by chromatography (silica gel:hexane:ethyl acetate/20:1)

Sources & evidence

ORD record
ord-f009dde34f134378b2812c5454d4a328
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Reaction notes

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