Nitrogen oxide (N2O4) → 3-Bromo-2-nitro-1-benzofuran

Reaction equation

[Br:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.[N+:11]([O-:16])([N+]([O-])=O)=[O:12]>>[Br:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[N+:11]([O-:16])=[O:12]

Participants

Reactant 2

HCID 25352Nitrogen oxide (N2O4)

HCID 6405893-Bromo-1-benzofuran

Product 1

HCID 135098423-Bromo-2-nitro-1-benzofuran

Procedure

To a stirred 80 g. sample of solid 3-bromobenzofuran is added a large excess of dinitrogen tetraoxide. The mixture liquifies within 5 minutes. After 2 hours, the mixture is triturated with ethanol and filtered to provide yellow crystals of 3-bromo-2-nitrobenzofuran. The product is identical to the product of Example 1 according to infrared spectral analysis.

Workup

waitAfter 2 hours
customthe mixture is triturated with ethanol
filtrationfiltered

Sources & evidence

ORD record: ord-b184488dbdaf49e1bc1525b04032eb7e
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04144347

Reaction notes

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