Sodium hydride → 5-Bromonicotinoyl chloride

HRID 555997Notes

Reaction equation

HRID 555997 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].[H-].[Na+].C(Cl)(=O)C([Cl:16])=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([Cl:16])=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 65578Oxalyl chlorideHCID 887075-Bromonicotinic acid

Product 1

HCID 27812235-Bromonicotinoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromonicotinic acid (1 g, 4.950 mmol) is placed in a 100 ml round bottomed flask and purged with Argon. Dry THF (20 ml) is added and the resulting solution is treated with NaH (60% dispersed in mineral oil) (0.202 g, 5.049 mmol) over a period of 5 minutes. The reaction mixture is stirred at room temperature for 10 minutes and then oxalyl chloride (0.453 ml, 5.198 mmol) is added slowly over 5 minutes followed by dry DMF (10 ul). The reaction mixture is stirred for a further 5 minutes, filtered through filter paper, concentrated in vacuo and dried under vacuum to afford the title compound.

Workup

  1. custompurged with Argon
  2. additionDry THF (20 ml) is added
  3. stirringThe reaction mixture is stirred for a further 5 minutes
  4. filtrationfiltered
  5. filtrationthrough filter paper
  6. concentrationconcentrated in vacuo
  7. customdried under vacuum

Sources & evidence

ORD record
ord-f22bf3ade78c4b9e99be7e50418f1474
Source dataset
uspto-grants-2011_11
Patent number
US08053574B2

Reaction notes

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