Ethanol → Ethyl 2-bromo-2-(4-chlorophenyl)acetate

HRID 354701Notes

Reaction equation

HRID 354701 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[Br:12]Br.[CH2:14](O)[CH3:15]>O>[Br:12][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:9]([O:11][CH2:14][CH3:15])=[O:10]

Participants

5

Reactant 3

HCID 702EthanolHCID 15880(4-Chlorophenyl)acetic acidHCID 24408Bromine2×

Product 1

HCID 228840Ethyl 2-bromo-2-(4-chlorophenyl)acetateYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chlorophenylacetic acid (34 g) and red phosphorus (1.5 g) was stirred under an atmosphere of nitrogen and dry bromine (20 g) was carefully added over a period of 30 minutes. The reaction mixture was heated to a temperature of 100° C. and dry bromine (32 g) was carefully added over a period of 45 minutes. The mixture was then heated under reflux for 3 hours and cooled. Ethyl alcohol (100 ml) was added to the reaction mixture and the mixture allowed to stand overnight. The ethanolic mixture was diluted with water and extracted with ethylene dichloride. The extract was washed with aqueous sodium carbonate, dried over anhydrous sodium sulfate and the solvent removed by distillation under reduced pressure. The product was distilled through a Fenske ring column to give ethyl α-bromo-4-chlorophenylacetate (33.4 g; 65%) b.p. 119° C. at 0.9 mm of Hg.

Workup

  1. additionwas carefully added over a period of 45 minutes
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux for 3 hours
  4. temperaturecooled
  5. extractionextracted with ethylene dichloride
  6. washThe extract was washed with aqueous sodium carbonate
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent removed by distillation under reduced pressure
  9. distillationThe product was distilled through a Fenske ring column

Sources & evidence

ORD record
ord-248a897fa1dd423bad2cb50bbe3f7ec8
Source dataset
uspto-grants-1983_03
Patent number
US04376784

Reaction notes

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