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

HRID 2164824Notes

Reaction equation

HRID 2164824 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-2ab10716d2424363b419b30ff41f31c5
Source dataset
uspto-grants-1985_03
Patent number
US04507317

Reaction notes

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