5-Chloro-2-methoxypyridine

Chemical Properties

Colorless to light yellow liquid

Uses

Reactant for:

• Preparation of biaryls via palladium-catalyzed Hiyama cross-coupling with aryltrifluorosilanes
• Suzuki-Miyaura cross-coupling reactions

Synthesis

16110-09-1

67-56-1

13473-01-3

1. Sodium hydride (60% dispersed in mineral oil, 5.50 g, 115 mmol, 2 eq.) was added in batches to dry methanol (distilled after treatment with magnesium strips, 25 mL) under nitrogen protection. 2. 2,5-Dichloropyridine (10.0 g, 68 mmol) was added to the above solution. 3. The reaction mixture was refluxed for 18 hours. 4. After completion of the reaction, the reaction was cooled to room temperature and treated with an excess of solid potassium bicarbonate. 5. and treated with excess solid potassium bicarbonate.5. The reaction mixture was filtered and the filtrate was concentrated to 50% of the original volume, at which point solids precipitated out of the solution.6. The solids were washed with hexane, and the washings were combined and concentrated to give the oily material.7. 2-methoxy-5-chloropyridine was purified by distillation under reduced pressure (102 °C, 2400 Pascals) to give 6.30 g (65% yield) as a colorless oily material. colorless oil. Mass spectra (chemical ionization, CH4) m/z: 144 (M+, 100), 146 (44), 172 (M+28, 19), 124 (9).

References

[1] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 8, p. 1245 - 1249
[2] Patent: US5512575, 1996, A