Selenium Dioxide → 5-Bromonaphthalene-1,2-dione

HRID 719164Notes

Reaction equation

HRID 719164 reaction equation
BrC1C=CC=CC=1CBr.[Br:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH2:13][CH2:14][CH2:15][C:16]2=[O:21].[Se](=O)=[O:23]>>[Br:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15](=[O:23])[C:16]2=[O:21]

Participants

4

Reactant 3

HCID 24007Selenium DioxideHCID 769652-Bromobenzyl bromideHCID 108895725-Bromo-1,2,3,4-tetrahydronaphthalen-1-one2×

Product 1

HCID 1880165-Bromonaphthalene-1,2-dione

Procedure

2-Bromobenzyl bromide was converted into 5-bromotetralone according to the literature (J. Org. Chem. 1984, p4226). Treatment of 5-bromotetralone with selenium dioxide as described in Referene Example 1A yielded 5-bromo-[1,2]naphthoquinone, which was coupled with 2,3-diamino-benzoic acid, diacetate salt, as described in Reference Example 1A to yield the title compound.

Sources & evidence

ORD record
ord-c6dac7f066b447849c3d94a1679e02dc
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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