N-bromobutanimide → Ethyl 2-(bromomethyl)-3-fluorobenzoate

HRID 477786Notes

Reaction equation

HRID 477786 reaction equation
[F:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[C:3]([CH2:13][Br:14])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 14626272Ethyl 3-fluoro-2-methylbenzoate

Product 1

HCID 14626273Ethyl 2-(bromomethyl)-3-fluorobenzoateYield 82.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 11 g of ethyl 3-fluoro-2-methylbenzoate in 300 ml of carbon tetrachloride is added 12 g of N-bromosuccinimide and the mixture is refluxed with heating for 12 hours. After cooling, the mixture is washed with water and a saturated saline solution and dried over magnesium sulfate and the solvent is distilled off under reduced pressure to give 13 g of ethyl 3-fluoro-2-bromomethylbenzoate. Mass spectrum m/z: 262, 260(M+).

Workup

  1. temperaturethe mixture is refluxed
  2. temperaturewith heating for 12 hours
  3. temperatureAfter cooling
  4. washthe mixture is washed with water
  5. dry with materiala saturated saline solution and dried over magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-44272f909ca047aca1e56cdfa6c427f5
Source dataset
uspto-grants-1989_12
Patent number
US04889858

Reaction notes

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