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

HRID 1995143Notes

Reaction equation

HRID 1995143 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:11][Br:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2318282-Bromo-3-nitrotoluene

Product 1

HCID 110663422-Bromo-1-bromomethyl-3-nitrobenzeneYield 90.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred solution of 1-bromo-2-methyl-6-nitrobenzene (16.2 g, 0.075 mole) in 200 ml of carbon tetrachloride was irradiated and heated at reflux with a 250 watt brooder lamp. N-bromosuccinimide (13.5 g, 0.075 mole) was added to the refluxing reaction mixture, and the mixture was stirred for approximately 23 hours. The mixture was cooled, filtered, and washed with two 200 ml portions of saturated aqueous sodium chloride solution. The organic phase was passed through phase separation filter paper. The filtrate was evaporated under reduced pressure to give 2-bromo-1-bromomethyl-3-nitrobenzene (20 g).

Workup

  1. temperatureheated
  2. temperatureat reflux with a 250 watt brooder lamp
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washwashed with two 200 ml portions of saturated aqueous sodium chloride solution
  6. customThe organic phase was passed through phase separation
  7. filtrationfilter paper
  8. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-663fdc46f08e42b3a6b0e9eba83ffc47
Source dataset
uspto-grants-1983_09
Patent number
US04402973

Reaction notes

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