Oxalyl chloride → 5-Bromo-2-chloro-3-pyridinecarbonyl chloride

HRID 1518509Notes

Reaction equation

HRID 1518509 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)(=O)C([Cl:15])=O>C(Cl)Cl.CN(C)C=O>[Br:1][C:2]1[CH:10]=[C:6]([C:7]([Cl:15])=[O:8])[C:5]([Cl:11])=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27633425-Bromo-2-chloronicotinic acid

Product 1

HCID 126772955-Bromo-2-chloro-3-pyridinecarbonyl chlorideYield 99.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a slurry of 5-bromo-2-chloronicotinic acid (2.063 g, 8.725 mmol) in methylene chloride (20 mL) was slowly added oxalyl chloride (1.11 g, 8.725 mmol) followed by the addition of dimethylformamide (5 drops). After 4H the mixture was concentrated in vacuo to provide 2.21 g of 5-bromo-2-chloropyridine-3-carbonyl chloride as a light brown solid, which was used as is in the next reaction.

Workup

  1. concentrationAfter 4H the mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-6c60691e92624cf885feaaa13f5d2984
Source dataset
uspto-grants-2012_07
Patent number
US08232406B2

Reaction notes

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