N-bromobutanimide → 1-Bromo-2-(bromomethyl)-3-nitrobenzene

HRID 1263161Notes

Reaction equation

HRID 1263161 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH2:11][Br:12]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1235372-Bromo-6-nitrotoluene

Product 1

HCID 150631701-Bromo-2-(bromomethyl)-3-nitrobenzeneYield 108.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 57.4 g (0.27 mole) of 2-bromo-6-nitro toluene in 800 ml of carbon tetrachloride was added 52.0 g (0.29 mole) of N-bromosuccinimide and 2.5 g of benzoyl peroxide. The mixture was heated to reflux for 64 hr., cooled and filtered. Removal of the solvent in vacuo afforded 86.1 g of a viscous oil. Purification was effected by washing through alumina (CCl4 /ether) and crystallization from ethyl alcohol; mp 61.5°-63°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 64 hr
  3. temperature, cooled
  4. filtrationfiltered
  5. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-4f6bb1b6be814bed873d3596c00aa93f
Source dataset
uspto-grants-1984_06
Patent number
USRE031617

Reaction notes

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