Chloride → N-(2-Bromo-4,6-difluorophenyl)-2,2-dimethylpropanamide

HRID 1637974Notes

Reaction equation

HRID 1637974 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[NH2:4].N1[CH:16]=[CH:15][CH:14]=CC=1.[Cl-].[CH2:18]([O:20]CC)C.Cl[CH2:24]Cl>CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[NH:4][C:18](=[O:20])[C:15]([CH3:14])([CH3:16])[CH3:24]

Participants

7

Reactant 5

HCID 312ChlorideHCID 1049PyridineHCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 1362852-Bromo-4,6-Difluoroaniline

Product 1

HCID 14141145N-(2-Bromo-4,6-difluorophenyl)-2,2-dimethylpropanamide

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

2-Bromo4,6-difluoroaniline (10.4 g, Aldrich) was dissolved in dichloromethane (75ml) and treated with pyridine (4.63 g) in an ice bath. 4-Dimethylaminopyridine (0.61 g) was then added and the mixture was allowed to warm to room temperature. After dropwise addition of pivotally chloride (7.23 g, BDH), the reaction was stirred for 5 hours. On completion, the mixture was added to diethyl ether (250 ml), washed twice with 2M HCl (250m1) and the resulting organic layer was treated with saturated NaHCO3 (2×250 ml). The organic layer was washed with water (250 ml), and dried over MgSO4. Removal of the solvent from the filtrate gave the crude title product as a white solid (13.40 g).

Workup

  1. washwashed twice with 2M HCl (250m1)
  2. additionthe resulting organic layer was treated with saturated NaHCO3 (2×250 ml)
  3. washThe organic layer was washed with water (250 ml)
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent from the filtrate

Sources & evidence

ORD record
ord-b471c04a707f46c6b7a4f563bcb9b87f
Source dataset
uspto-grants-2000_03
Patent number
US06043284

Reaction notes

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