Pyridine → N-(4-bromo-3-chloro-2-fluorophenyl)acetamide

HRID 1967315Notes

Reaction equation

HRID 1967315 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[C:3]=1[Cl:10].[C:11](OC(=O)C)(=[O:13])[CH3:12].N1C=CC=CC=1>C(OCC)(=O)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:11](=[O:13])[CH3:12])=[C:4]([F:9])[C:3]=1[Cl:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 27827054-Bromo-3-chloro-2-fluoroaniline

Product 1

HCID 23273791N-(4-bromo-3-chloro-2-fluorophenyl)acetamideYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4-bromo-3-chloro-2-fluoroaniline (15.0 g) in ethyl acetate (200 mL) was added dropwise acetic anhydride (7.57 mL) at 0° C. Then, pyridine (10.8 mL) was added dropwise, and the mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate, washed with water and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained solid was washed with hexane to give the title compound as a colorless solid (yield: 17.1 g, 96%).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. washThe obtained solid was washed with hexane

Sources & evidence

ORD record
ord-cfa4ece443a64a96a7cf4d955a7eaaa4
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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