N-bromobutanimide → Methyl 3-(bromomethyl)-2,4-dichlorobenzoate

HRID 1368820Notes

Reaction equation

HRID 1368820 reaction equation
[Cl:1][C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:14][CH2:12][C:11]1[C:2]([Cl:1])=[C:3]([CH:8]=[CH:9][C:10]=1[Cl:13])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 21941248HCID 21941248, compound

Product 1

HCID 15477480Methyl 3-(bromomethyl)-2,4-dichlorobenzoateYield 95.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

1.0 g of azobisisobutyronitrile was added to a solution of 84.0 g (0.38 mol) of methyl 2,4-dichloro-3-methylbenzoate and 67.6 g (0.38 mol) of N-bromosuccinimide in 380 ml of carbon tetrachloride. After heating for 3.5 hours under reflux, the reaction mixture was cooled and the resulting precipitate was filtered off with suction. The filtrate was concentrated under reduced pressure and the resulting residue was triturated with methyl tert-butyl ether. 108.0 g of methyl 3-bromomethyl-2,4-dichlorobenzoate were obtained.

Workup

  1. temperatureAfter heating for 3.5 hours
  2. temperatureunder reflux
  3. temperaturethe reaction mixture was cooled
  4. filtrationthe resulting precipitate was filtered off with suction
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was triturated with methyl tert-butyl ether

Sources & evidence

ORD record
ord-65fa1a9b0dd94e99b5ffdfcec4910b02
Source dataset
uspto-grants-2003_06
Patent number
US06576596B1

Reaction notes

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