Benzoyl Peroxide → Ethyl 2-bromo-2-(3,4-dichlorophenyl)acetate

HRID 2048992Notes

Reaction equation

HRID 2048992 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[Br:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:15][CH:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2737422Ethyl 3,4-dichlorophenylacetate

Product 1

HCID 12717583Ethyl 2-bromo-2-(3,4-dichlorophenyl)acetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In a three-necked flask fitted with a Nichrome stirrer and a reflux condenser is placed 7.0 g of ethyl 3,4-dichlorophenylacetate, 5.9 g of N-bromosuccinimide, 0.1 g of benzoyl peroxide and 150 ml of carbon tetrachloride. The reaction mixture is heated at reflux for 18 hours, cooled and filtered. The carbon tetrachloride filtrate is concentrated under reduced pressure to give a deep orange liquid. Vacuum distillation at 115°-120° C. (0.5 mm) gives ethyl α-bromo-3,4-dichlorophenylacetate as a pale yellow liquid.

Workup

  1. customIn a three-necked flask fitted with a Nichrome stirrer and a reflux condenser
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 18 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. concentrationThe carbon tetrachloride filtrate is concentrated under reduced pressure
  7. customto give a deep orange liquid
  8. distillationVacuum distillation at 115°-120° C. (0.5 mm)

Sources & evidence

ORD record
ord-5e599ca3fbc74311aedf34fa5f069221
Source dataset
uspto-grants-1980_04
Patent number
US04196120

Reaction notes

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