Benzoyl Peroxide → 2-(Bromomethyl)-5-nitro-1-benzofuran

HRID 1761876Notes

Reaction equation

HRID 1761876 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[O:11][C:12]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:13]=2[CH:14]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:9][C:10]1[O:11][C:12]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:13]=2[CH:14]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 44874532-Methyl-5-nitrobenzofuran

Product 1

HCID 114141792-(Bromomethyl)-5-nitro-1-benzofuran

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (1.1 g, 6.2 mmole) was added portionwise to a solution of 2-methyl-5-nitrobenzofuran (1.0 g, 5.6 mmole) and benzoyl peroxide (50 mg) in carbon tetrachloride (50 ml) and the reaction mixture was heated at reflux temperature for 6 hours in the presence of bright light. The reaction mixture was then cooled, filtered and the filtrate evaporated to dryness. The residue was recrystallised from petroleum ether to give the title compound, yield 0.75 g, m.p. 96°-98°.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature for 6 hours in the presence of bright light
  3. temperatureThe reaction mixture was then cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated to dryness
  6. customThe residue was recrystallised from petroleum ether

Sources & evidence

ORD record
ord-203b454e71ed43f78489ae84649a450a
Source dataset
uspto-grants-1989_05
Patent number
US04829071

Reaction notes

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