2-Chloro-4'-fluoroacetophenone → 2-(4-Fluorophenyl)-2-oxoethyl acetate

HRID 467454Notes

Reaction equation

HRID 467454 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:4].[C:12]([O-:15])(=[O:14])[CH3:13].[Na+]>CN(C)C=O>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][O:15][C:12](=[O:14])[CH3:13])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1202482-Chloro-4'-fluoroacetophenoneHCID 517045Sodium Acetate

Product 1

HCID 125235892-(4-Fluorophenyl)-2-oxoethyl acetateYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a 3 liter flask were added 400 grams (2.32 mol) 2-chloro-1-(4-fluorophenyl)ethanone, 1 liter of N,N-dimethylformamide and 265 grams (3.23 mol) anhydrous sodium acetate. The mixture was stirred and heated to 90° C., and the reaction lasted 10 hours. After the reaction was completed, the heating was stopped. The reaction solution was cooled down to room temperature, and extracted with ethyl acetate (600 ml×6). The organic phases were combined, washed three times with brine, dried over anhydrous sodium sulfate and concentrated until dry. The residue was crystallized from the mixed toluene/petroleum ether solution and dried to obtain 357 grams (1.82 mol) compound A-1 with yield of 78.5%. 1H NMR (400 MHz, CDCl3): δ 2.23 (s, 3H, CH3), 5.30 (s, 2H, —CH2—), 7.14-7.19 (m, 2H, Cpr-H), 7.93-7.97 (m, 2H, Cpr-H); MS (m/z): 197 [M+H].

Workup

  1. temperatureThe reaction solution was cooled down to room temperature
  2. extractionextracted with ethyl acetate (600 ml×6)
  3. washwashed three times with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customuntil dry
  7. customThe residue was crystallized from the mixed toluene/petroleum ether solution
  8. customdried

Sources & evidence

ORD record
ord-8d0f7b3c6e2c45ed8a44cc095c9196d5
Source dataset
uspto-grants-2014_01
Patent number
US08623855B2

Reaction notes

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