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

HRID 66285

Reaction equation

HRID 66285 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-8bb4d254d7f440ec8351d60f1eca7e2b
Source dataset
uspto-grants-1978_12
Patent number
US04131611

Linked notes

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