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

HRID 2177057

Reaction equation

HRID 2177057 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-254c1c65fedf4bc7b980642b38967d0e
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Linked notes

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