Benzoyl Peroxide → Ethyl 2-(bromomethyl)benzoate

HRID 1374829Notes

Reaction equation

HRID 1374829 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11])[CH3:2].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CCCCCC>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][Br:13])[CH3:2]

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 8058HexaneHCID 66598Ethyl 2-methylbenzoateHCID 67184N-bromobutanimide

Product 1

HCID 11032082Ethyl 2-(bromomethyl)benzoateYield 109.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Methylbenzoic acid ethyl ester (2.00 g, 11.9 mmol) was dissolved in carbon tetrachloride (60 ml), and the solution was added with N-bromosuccinimide (2.56 g, 14.4 mmol) and a catalytic amount of benzoylperoxide and then heated under reflux. After one hour, the reaction mixture was cooled to room temperature and added with hexane (40 ml) to remove insoluble solids by filtration. The filtrate was evaporated under reduced pressure to obtain the title compound 3.16 g as yellow oil. the product was used in the next reaction without purification.

Workup

  1. temperatureunder reflux
  2. customto remove insoluble solids
  3. filtrationby filtration
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7dfa3f50424d46a3b87f7c37f315d4a6
Source dataset
uspto-grants-2007_01
Patent number
US07166617B2

Reaction notes

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