Ethyl 2-methylbenzoate → Ethyl 2-(bromomethyl)benzoate

HRID 1388814Notes

Reaction equation

HRID 1388814 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 66598Ethyl 2-methylbenzoateHCID 67184N-bromobutanimide

Product 1

HCID 11032082Ethyl 2-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred mixture of ethyl 2-methylbenzoate (30 grams, 0.183 mole) and N-bromosuccinimide (35 grams, 0.194 mole) in carbon tetrachloride (200 ml) was irradiated with an infrared lamp and heated at reflux for 20 minutes. The reaction mixture was allowed to cool to room temperature, then filtered. The filtrate was evaporated under reduced pressure to give ethyl 2-bromomethylbenzoate as a yellow oil.

Workup

  1. customwas irradiated with an infrared lamp
  2. temperatureheated
  3. temperatureat reflux for 20 minutes
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2bee7a0bd7ab484cb39b5158410d5c3b
Source dataset
uspto-grants-1984_02
Patent number
US04433182

Reaction notes

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