Methyl iodide → Methyl 6-bromopyridine-2-carboxylate

HRID 853765Notes

Reaction equation

HRID 853765 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[C:11](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.ClCCl>[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5939196-Bromopyridine-2-carboxylic acid

Product 1

HCID 16217886Methyl 6-bromopyridine-2-carboxylateYield 82.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

6-bromopicolinic acid (1.99 g) in DMF (10 mL) was treated with potassium carbonate (1.40 g) and then methyl iodide (4 mL) at room temperature for 20 h. The reaction mixture was diluted with dichloromethane (60 mL) and filtered. The filtrate was extracted with brine (twice), dried (MgSO4), and concentrated under vacuum to give methyl 6-bromopicolinate as a pale yellow solid (1.75 g).

Workup

  1. filtrationfiltered
  2. extractionThe filtrate was extracted with brine (twice),
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ceb6d0b498cc4bc49efc07039e6520c3
Source dataset
uspto-grants-2007_08
Patent number
US07256186B2

Reaction notes

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