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

HRID 459782

Reaction equation

HRID 459782 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 80%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 1-bromo-2-methyl-3-nitro-benzene (16.095 g, 74.5 mmol), 1-Bromo-pyrrolidine-2,5-dione (13.26 g, 74.5 mmol), benzoyl peroxide(180 mg, 0.74 mmol) in CCl4 (100 ml) was heated under reflux overnight. After removing the solvent by using rotary evaporator, the residue was partitioned between water and ethyl acetate. The organic layer was washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and resulting brown residue was purified by flash chromatography to give 1-bromo-2-bromomethyl-3-nitro-benzene as a yellow solid (17.55 g, 80%). 1H NMR (CDCl3, 300 MHz) δ: 4.89(s, 2H), 7.35(dd, 1H, J1=J2=8.1 Hz), 7.88(dd, 2H, J1=1.6 Hz, J2=8.1 Hz).

Workup

  1. temperatureunder reflux overnight
  2. customAfter removing the solvent
  3. customevaporator
  4. customthe residue was partitioned between water and ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialAfter drying over MgSO4
  7. concentrationthe organic fraction was concentrated in vacuo
  8. customresulting brown residue
  9. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-151e37554eae42eb96c1cf06ba873b9e
Source dataset
uspto-grants-2007_03
Patent number
US07196087B2

Linked notes

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