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

HRID 1372498Notes

Reaction equation

HRID 1372498 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Br:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([F:16])[CH:10]=1>N1C=CC=CC=1>[Br:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[C:11]([F:16])[CH:10]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 4149902N-(4-bromo-2-fluorophenyl)-2,2-dimethylpropanamideYield 86.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Pivaloyl chloride (72 mL, 580 mmol) was added slowly (caution—exothermic reaction) to an ice cold solution of 4-bromo-2-fluoroaniline (100 g, 526 mmol) in pyridine (200 mL). After the addition, the ice bath was removed and the hot reaction mixture was stirred at room temperature for 30 minutes. The mixture was poured into cold water (500 mL) and the precipitated product was collected by filtration and washed with 1N HCl. The solid was dissolved in EtOAc (1 L), dried over MgSO4, filtered, and concentrated under vacuum to provide N-(4-bromo-2-fluorophenyl)-2,2-dimethylpropanamide (125 g).

Workup

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. additionThe mixture was poured into cold water (500 mL)
  4. filtrationthe precipitated product was collected by filtration
  5. washwashed with 1N HCl
  6. dissolutionThe solid was dissolved in EtOAc (1 L)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6de521c88d12476d91f74f25aca89deb
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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