Nitric Acid → 3-Bromo-2-nitro-1-benzofuran

HRID 614358

Reaction equation

HRID 614358 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-])([OH:13])=[O:12].N([O-])=O.[Na+]>CO>[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-:13])=[O:12]

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 6405893-Bromo-1-benzofuranHCID 23668193Sodium Nitrite

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 5.0 g. sample of powdered 3-bromobenzofuran on a glass dish is placed next to a container of nitric acid. Sodium nitrite is added periodically to the nitric acid, and the entire experiment is covered with a bell jar. After about 15 minutes the powder becomes an oil. After 12 hours the product is dissolved in hot methanol and slowly crystallized by cooling. Recrystallization from methanol provides yellow crystals of 3-bromo-2-nitrobenzofuran, m.p. 130°-132° C. (lit. 132° C.).

Workup

  1. customslowly crystallized
  2. temperatureby cooling
  3. customRecrystallization from methanol

Sources & evidence

ORD record
ord-e8b879d8638c47dbba8295506a30c2d9
Source dataset
uspto-grants-1979_03
Patent number
US04144347

Linked notes

Loading…