反应详情

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.

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