Benzoyl Peroxide → Ethyl 4-(bromomethyl)-2-chlorobenzoate

HRID 1904413Notes

Reaction equation

HRID 1904413 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:11]1[CH:10]=[CH:9][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([Cl:1])[CH:12]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 14459377Benzoic acid, 2-chloro-4-methyl-, ethyl ester

Product 1

HCID 14459378Ethyl 4-(bromomethyl)-2-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of ethyl 2-chloro-4-methylbenzoate (2.34 g, 0.0118 mol), N-bromosuccinimide (2.05 g, 0.0115 mol), and benzoyl peroxide (0.5 g) in carbon tetrachloride (50 ml) was heated under reflux for 90 minutes. The resulting solution was filtered and the solvent was evaporated off under reduced pressure to yield ethyl 4-(bromomethyl)-2-chlorobenzoate as a yellow crystalline solid having the following structural characteristics:

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 90 minutes
  3. filtrationThe resulting solution was filtered
  4. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-144559fac48f445fa7c30663345cfb4e
Source dataset
uspto-grants-1989_06
Patent number
US04837333

Reaction notes

Loading…