Water → 2-chloro-N-(4-fluorophenyl)acetamide

HRID 1374836Notes

Reaction equation

HRID 1374836 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[F:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1.O>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]([NH:11][C:10]1[CH:12]=[CH:13][C:7]([F:6])=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 97314-Fluoroaniline

Product 1

HCID 5320652-chloro-N-(4-fluorophenyl)acetamideYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Chloroacetyl chloride (0.60 ml, 7.54 mmol) was dissolved in toluene (6 ml), and the solution was added with 4-fluoroaniline (0.72 ml, 7.52 mmol) at room temperature and stirred at the same temperature for 1 hour. The reaction mixture was added with water and extracted with ethyl acetate, and the extract was washed with saturated brine and dried over magnesium sulfate. Insoluble solids were removed by filtration and the filtrate was evaporated under reduced pressure to obtain the title compound as pale yellow solid (1.07 g, yield: 76%).

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customInsoluble solids were removed by filtration
  5. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ddcd701c70e74d6b80e7ebecdca7c2ef
Source dataset
uspto-grants-2007_01
Patent number
US07166617B2

Reaction notes

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