Pivaloyl chloride → N-(4-bromo-2-fluorophenyl)-2,2-dimethylpropanamide

HRID 1736252Notes

Reaction equation

HRID 1736252 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[C:10](Cl)(=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12]>N1C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([F:9])[CH:3]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 4149902N-(4-bromo-2-fluorophenyl)-2,2-dimethylpropanamideYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

250 g (1.32 mol) of 4-bromo-2-fluoroaniline was dissolved in 500 mL of pyridine, 178 mL (1.45 mol) of pivaloyl chloride was added dropwise under ice-cooling, and the mixture was stirred for 10 minutes. The reaction solution was poured into 1.5 L of ice-water and the precipitated crystals were collected by filtration. The crystals were washed with 1N HCl and water, and dried under reduced pressure, to give 350 g of 4-bromo-2-fluoro-N-pivaloylaniline (yield: 97%).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated crystals were collected by filtration
  3. washThe crystals were washed with 1N HCl and water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-814bd2abb7ed42d4b85963fa473da3c8
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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