N-bromobutanimide → Methyl 4-(bromomethyl)-3-chlorobenzoate

HRID 439784Notes

Reaction equation

HRID 439784 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[Cl:12].[Br:13]N1C(=O)CCC1=O.C1C(C(OOOC(=O)C2C=CC=CC=2)=O)=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[Cl:12]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 2801405Methyl 3-Chloro-4-methylbenzoateHCID 53400210Perbenzoic anhydride

Product 1

HCID 22027761Methyl 4-(bromomethyl)-3-chlorobenzoateYield 75%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl 4-methyl-3-chlorobenzoate (4.5 g, 0.024 mol) was dissolved in carbon tetrachloride (100 ml), and thereto were added N-bromosuccinimide (4.8 g, 0.026 mol) and a catalytic amount of perbenzoic anhydride. The mixture was heated and refluxed under nitrogen atmosphere for 2 hours, allowed to cool, and the precipitate was separated by filtration. The filtrate was concentrated, and separated and purified by using a silica-gel column chromatography (ethyl acetate:n-hexane=1:20) to give the title compound (4.7 g, 0.018 mol) (yield 75%).

Workup

  1. temperatureThe mixture was heated
  2. temperaturerefluxed under nitrogen atmosphere for 2 hours
  3. temperatureto cool
  4. customthe precipitate was separated by filtration
  5. concentrationThe filtrate was concentrated
  6. customseparated
  7. custompurified

Sources & evidence

ORD record
ord-9f521ed4bd8a4df6aa4527703552590e
Source dataset
uspto-grants-1996_05
Patent number
US05516777

Reaction notes

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