Acetic Acid → 2-(4-Chlorophenyl)-2-oxoethyl acetate

HRID 1364479Notes

Reaction equation

HRID 1364479 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1Br)=[O:3].[C:12]([OH:15])(=[O:14])[CH3:13].C(N(CC)CC)C>C(#N)C>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH2:1][O:15][C:12](=[O:14])[CH3:13])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8471TriethylamineHCID 47126441-(2-Bromo-4-chlorophenyl)ethanone

Product 1

HCID 5872542-(4-Chlorophenyl)-2-oxoethyl acetateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
4 °C

Procedure

To a cooled (4° C.) and stirred solution of 2-bromo-4-chloroacetophenone (5.0 g, 21.41 mmol) and glacial acetic acid (2.8 mL, 49.25 mmol) in acetonitrile was added triethylamine (6.1 mL, 44.97 mmol). The reaction mixture was warmed to room temperature, than refluxed for 3 hours. The reaction mixture was extracted with ether, acetate, washed with 1N hydrochloric acid, brine, dried, and concentrated to yield 4.1 g of acetic acid 2-(4-chlorophenyl)-2-oxo-ethyl ester.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. temperaturethan refluxed for 3 hours
  3. extractionThe reaction mixture was extracted with ether, acetate
  4. washwashed with 1N hydrochloric acid, brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-519aa66d13344181be664316a80c9309
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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