Water → 6-(4-Iodo-phenoxymethyl)-pyridine-2-carboxylic acid methyl ester

HRID 2113000Notes

Reaction equation

HRID 2113000 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11]Br)[N:6]=1)=[O:4].[I:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:20][C:17]2[CH:18]=[CH:19][C:14]([I:13])=[CH:15][CH:16]=2)[N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 21471714Methyl 6-(bromomethyl)pyridine-2-carboxylate

Product 1

HCID 576433496-(4-Iodo-phenoxymethyl)-pyridine-2-carboxylic acid methyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

6-Bromomethyl-pyridine-2-carboxylic acid methyl ester (2.27 g, 9.9 mmol; from Step 2 above) was dissolved in acetone (50 mL) and 4-iodophenol (2.37 g, 10.8 mmol; available from Aldrich Chemical Company, Inc., Milwaukee, Wis.) was added, followed by finely ground potassium carbonate (1.54 g, 11.2 mmol). The mixture was heated overnight at 60 degrees, and it was then cooled and filtered. The solid was washed with acetone and the filtrate was concentrated to dryness. Ethyl acetate (100 mL) was added and the solution was washed twice with 2 M NaOH, with water, and with brine. The solution was dried (magnesium sulfate), filtered and evaporated to give the crude product. This was dissolved in acetone (approximately 25 mL) with warming, and water (approximately 20 mL) was added. An oil came out of solution and it crystallized. The mixture was heated to redissolve the solid and the solution was seeded with a crystal of the product to give crystals of the product. The recrystallization was repeated to give 6-(4-iodo-phenoxymethyl)-pyridine-2-carboxylic acid methyl ester (2.24 g, 62%) as a white crystalline solid. Mass spectrum m/z 370.

Workup

  1. temperatureThe mixture was heated overnight at 60 degrees
  2. temperatureit was then cooled
  3. filtrationfiltered
  4. washThe solid was washed with acetone
  5. concentrationthe filtrate was concentrated to dryness
  6. additionEthyl acetate (100 mL) was added
  7. washthe solution was washed twice with 2 M NaOH, with water
  8. dry with materialThe solution was dried (magnesium sulfate)
  9. filtrationfiltered
  10. customevaporated
  11. customto give the crude product
  12. temperaturewith warming
  13. customcrystallized
  14. temperatureThe mixture was heated
  15. dissolutionto redissolve the solid
  16. customto give crystals of the product
  17. customThe recrystallization

Sources & evidence

ORD record
ord-abb1f7e0243f46219ffe6a1ed6ef4539
Source dataset
uspto-grants-2009_04
Patent number
US07524870B2

Reaction notes

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