Juglone → 1,4-Naphthalenedione, 2-bromo-8-hydroxy-

HRID 2369451Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:13])[CH:5]=[CH:6][C:7]2=[O:12].[Br:14]Br>>[CH:10]1[CH:11]=[C:2]([OH:1])[C:3]2[C:4]([C:5]([Br:14])=[CH:6][C:7](=[O:12])[C:8]=2[CH:9]=1)=[O:13]

Participants

Reactant 2

HCID 3806Juglone

HCID 24408Bromine

Product 1

HCID 9275141,4-Naphthalenedione, 2-bromo-8-hydroxy-

Procedure

Step 1 in the above Scheme B may be, for example, carried out according to Tietze, et al., Chem. Eur. J., 2007, 13, 9939-9947. For example, to 5-hydroxynaphthalene-1,4-dione dissolved in an appropriate solvent is added bromine to give 3-bromojuglone in Step 1.

Sources & evidence

ORD record: ord-bca9f7afd4404640918af23cd0661eaa
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703979B2

Reaction notes

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