N-bromobutanimide → 2-(Bromomethyl)-5-nitro-1-benzofuran

HRID 1031969Notes

Reaction equation

HRID 1031969 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(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[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 2

HCID 67184N-bromobutanimideHCID 44874532-Methyl-5-nitrobenzofuran

Product 1

HCID 114141792-(Bromomethyl)-5-nitro-1-benzofuranYield 52.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 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-0d038d9c805a400ca24251c2cd089f6b
Source dataset
uspto-grants-1990_09
Patent number
US04956382

Reaction notes

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