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

HRID 2414259Notes

Reaction equation

HRID 2414259 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O>N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[Cl:1])[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 7015786Benzoic acid, 4-chloro-3-methyl-, methyl ester

Product 1

HCID 12144656Methyl 3-(bromomethyl)-4-chlorobenzoateYield 59.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

40.4 g of methyl 4-chloro-3-methylbenzoate, 39 g of N-bromosuccinimide and 1 g of azobisisobutyronitrile were added to 300 ml of carbon tetrachloride, followed by reflux under heating for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, insoluble matters were collected by filtration and the filtrate was concentrated. The obtained crude crystals were washed with hexane to obtain 34.3 g of methyl 3-bromomethyl-4-chlorobenzoate as white crystals.

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 4 hours
  3. customAfter completion of the reaction
  4. filtrationinsoluble matters were collected by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe obtained crude crystals
  7. washwere washed with hexane

Sources & evidence

ORD record
ord-ced7b1884ccd4a3685a8f5369d7bdf31
Source dataset
uspto-grants-2004_11
Patent number
US06812229B1

Reaction notes

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