Methyl iodide → Methyl 6-bromopyridine-2-carboxylate

HRID 1272513Notes

Reaction equation

HRID 1272513 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-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Treat 6-bromopicolinic acid (1.99 g) in DMF (10 mL) with potassium carbonate (1.40 g) and then methyl iodide (4 mL) at room temperature for 20 h. Dilute the reaction mixture with dichloromethane (60 mL) and filter. Extract the filtrate with brine (twice), dry (MgSO4), and concentrate in vacuo to give methyl 6-Bromopicolinate pale yellow solid (1.75 g).

Workup

  1. filtrationfilter
  2. extractionExtract the filtrate with brine (twice),
  3. dry with materialdry (MgSO4)
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-02f9b0d8750b422cb3820e924d6e426a
Source dataset
uspto-grants-2007_04
Patent number
US07208602B2

Reaction notes

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