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

HRID 253955Notes

Reaction equation

HRID 253955 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 4 H 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 4 H the mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ce0e654bb026495fb66ba32c6d8ce0c5
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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