2,6-Dibromo-4-methoxypyridine Chemical Properties

Melting point:

136 °C(Solv: ethanol (64-17-5); water (7732-18-5))

Boiling point:

283.0±35.0 °C(Predicted)

Density 

1.919±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

crystalline solid

pka

-2.35±0.10(Predicted)

color 

Lemon

Safety Information

HS Code 

2933399990

2,6-Dibromo-4-methoxypyridine Usage And Synthesis

Uses

2,6-Dibromo-4-methoxypyridine is a useful reactant for the preparation of various organic compounds such as pyridine-pyridone alternate oligomers, and cyclic adenosine monophosphate.

Synthesis

Reaction of 2,4,6-tribromopyridine (5) and sodium methanol (1.2 eq.) under methanol reflux conditions afforded 2,6-dibromo-4-methoxypyridine (6) in 80% yield. Subsequently, the compound (6) was treated with n-butyllithium (1.2 eq.) at -78 °C and reacted with pivaleronitrile (1.2 eq.) for 150 min, followed by refluxing in two conventional sulfuric acids for 2 h to afford the keto isomer (7) in 86% yield. Compound (7) was converted to optically active alcohol (8) in 93% yield and 90% optical purity by hydrogen transfer type asymmetric reduction catalyzed by asymmetric ruthenium catalyst RuCl[(S,S)-Tddpen] (p-isopropylbenzene, 0.01 equiv.) using formic acid (4.3 equiv.) and triethylamine (2.5 equiv.). Next, compound (8) was converted to a camphor ester using a chloride, processed for optical splitting by recrystallization (75% yield, diastereoisomer ratio = 99/<1), and saponified again to give an almost optically pure alcohol (7, quantitatively). Finally, homogeneous coupling of compound (7) using palladium catalyst [PdCl2(PhCN)2-TDAE] afforded the pyridine isomer (9) (chemical formula 5) in 36% yield (diastereoisomer ratio = >99.5/<0.5).

References

[1] Patent: EP1724251, 2006, A1. Location in patent: Page/Page column 5; 9

2,6-Dibromo-4-methoxypyridine(117873-72-0)Related Product Information

• 2-BROMO-4-HYDROXYPYRIDINE
• 2-Bromo-4-methoxypyridine
• 2,6-Dibromo-4-methoxypyridine
• 2,3,6-TRIBROMO-4-METHOXY-5-NITROPYRIDINE