Oxalyl chloride → 5-Bromo-pyridine-2-carbonyl chloride

HRID 534753

Reaction equation

HRID 534753 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.C(Cl)(=O)C([Cl:14])=O>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([Cl:14])=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 6085445-Bromopyridine-2-carboxylic acid

Product 1

HCID 190907715-Bromo-pyridine-2-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

The acid from step 1 (0.702 g, 3.475 mmol) was suspended in DCM (40 mL) under argon, DMF (1 drop) was added and the mixture was cooled in an ice-bath. Oxalyl chloride was added portion-wise over 5 minutes and the mixture was then heated to 40° C. for 90 minutes. On cooling, the solvent was removed to produce 5-bromo-2-pyridinecarbonyl chloride (0.801 g) as a brown solid which was used in step 3.

Workup

  1. temperaturethe mixture was cooled in an ice-bath
  2. temperatureOn cooling
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-a23c7d8561344844955800d53c2c43f4
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Linked notes

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