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

HRID 345032Notes

Reaction equation

HRID 345032 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-ca4cca6f499844f78260077a2583c2bf
Source dataset
uspto-grants-1991_10
Patent number
US05055473

Reaction notes

Loading…