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

HRID 1856630Notes

Reaction equation

HRID 1856630 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. The reaction mixture was refluxed for 3.5 hours and then cooled, and the precipitate which had formed was filtered off with suction. The filtrate was concentrated under reduced pressure and the resulting residue was triturated with methyl t-butyl ether. 108.0 g of methyl 3-bromomethyl-2,4-dichlorobenzoate were obtained.

Workup

  1. temperatureThe reaction mixture was refluxed for 3.5 hours
  2. temperaturecooled
  3. customthe precipitate which had formed
  4. filtrationwas filtered off with suction
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was triturated with methyl t-butyl ether

Sources & evidence

ORD record
ord-c0743e5ec24e467fa47614f89d3843dc
Source dataset
uspto-grants-2000_11
Patent number
US06143696

Reaction notes

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