Acetyl chloride → 4'-Chloro-2'-fluoroacetanilide

HRID 725234Notes

Reaction equation

HRID 725234 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([F:13])[CH:7]=1.C(N(CC)CC)C.C(OCC)(=O)C>O1CCCC1.C(O)C>[Cl:5][C:6]1[CH:12]=[CH:11][C:9]([NH:10][C:1](=[O:3])[CH3:2])=[C:8]([F:13])[CH:7]=1

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 938984-Chloro-2-fluoroaniline

Product 1

HCID 8531744'-Chloro-2'-fluoroacetanilide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (24.2 mL, 0.34 mol) is added slowly to a solution of 4-chloro-2-fluoroaniline (49.4 g, 0.34 mol), and triethylamine (47 mL, 0.34 mol) in tetrahydrofuran while maintaining the reaction mixture temperature below 20° C. After the addition is complete, the reaction mixture is stirred overnight at room temperature, and poured into ethyl acetate. The organic solution is washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an off-white solid. A mixture of the solid in ethanol is stirred for several minutes, and filtered to give the tilte product as a white solid.

Workup

  1. temperaturewhile maintaining the reaction mixture temperature below 20° C
  2. additionAfter the addition
  3. washThe organic solution is washed sequentially with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain an off-white solid
  7. stirringis stirred for several minutes
  8. filtrationfiltered

Sources & evidence

ORD record
ord-4874f450c78c4111a5ea8c4c52c6282b
Source dataset
uspto-grants-1998_01
Patent number
US05705644

Reaction notes

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