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

HRID 1955652Notes

Reaction equation

HRID 1955652 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[NH2:4].N1C=CC=CC=1.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19].C(OCC)C>ClCCl.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:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 62493Pivaloyl chlorideHCID 1362852-Bromo-4,6-Difluoroaniline

Product 1

HCID 14141145N-(2-Bromo-4,6-difluorophenyl)-2,2-dimethylpropanamideYield 91.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Bromo-4,6-difluoroaniline (10.4 g, Aldrich) was dissolved in dichloromethane (75 ml) 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 warn to room temperature. After dropwise addition of pivaloyl 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 HCI (250 ml) 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. customto warn to room temperature
  2. washwashed twice with 2M HCI (250 ml)
  3. additionthe resulting organic layer was treated with saturated NaHCO3 (2×250 ml)
  4. washThe organic layer was washed with water (250 ml)
  5. dry with materialdried over MgSO4
  6. customRemoval of the solvent from the filtrate

Sources & evidence

ORD record
ord-5980787821544ef39197c193d7926f4d
Source dataset
uspto-grants-1998_07
Patent number
US05776951

Reaction notes

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