Pivaloyl chloride → 4-bromo-2,6-dichloro-N-pivaloylaniline

HRID 1736242Notes

Reaction equation

HRID 1736242 reaction equation
Cl.[Br:2][C:3]1[CH:9]=[C:8]([Cl:10])[C:6]([NH2:7])=[C:5]([Cl:11])[CH:4]=1.[C:12](Cl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]>N1C=CC=CC=1>[Br:2][C:3]1[CH:9]=[C:8]([Cl:10])[C:6]([NH:7][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[C:5]([Cl:11])[CH:4]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 194349524-Bromo-2,6-dichloroaniline hydrochloride

Product 1

HCID 194349714-bromo-2,6-dichloro-N-pivaloylanilineYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

12.0 g (50.0 mmol) of 4-bromo-2,6-dichloroaniline hydrochloride was dissolved in 50 mL of pyridine, 9.90 mL (80.0 mmol) of pivaloyl chloride and 0.61 g (5.0 mmol) of N,N-dimethylaminopyridine were added and the mixture was stirred at 40° C. for 28 hours. Thereafter, substantially the same manner as that in Reference Example (1) was repeated to give 15.7 g of 4-bromo-2,6-dichloro-N-pivaloylaniline (yield: 97%).

Sources & evidence

ORD record
ord-a263e0617b6d4bc99550e0abe3446c07
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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