3-Bromo-5-ethoxypyridine

3-Bromo-5-ethoxypyridine Property

Melting point:

9°C(lit.)

Boiling point:

240°C(lit.)

refractive index 

1.5540 to 1.5580

storage temp. 

Inert atmosphere,Room Temperature

form 

clear liquid

color 

Colorless to Light orange to Yellow

Safety

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H317May cause an allergic skin reaction

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

3-Bromo-5-ethoxypyridine Chemical Properties,Usage,Production

Synthesis

Sodium metal (4.60 g, 200 mmol) was added in batches to anhydrous ethanol (100 mL) under nitrogen protection, keeping the reaction temperature at 0-5 °C. The mixture was stirred to slowly warm up to room temperature over 18 hours. Subsequently, 3,5-dibromopyridine (31.5 g, 133 mmol) and N,N-dimethylformamide (DMF, 100 mL) were added to the reaction system. The reaction mixture was heated to 70 °C with continuous stirring for 48 hours. After completion of the reaction, the brown mixture was cooled to room temperature, slowly poured into water (600 mL) and extracted with ether (3 x 500 mL). The ether extracts were combined, dried with anhydrous sodium sulfate, filtered and concentrated by rotary evaporator. The final product was purified by vacuum distillation to give 22.85 g (85.0% yield) of 5-bromo-3-ethoxypyridine as an oil with a boiling point of 89-90 °C (2.8 mmHg). A boiling point of 111 °C (5 mmHg) has been reported in the literature (see K. Clarke et al., J. Chem. Soc. 1885 (1960)).

References

[1] Patent: WO2006/23630, 2006, A2. Location in patent: Page/Page column 60
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4126 - 4141
[3] Patent: WO2010/96389, 2010, A1. Location in patent: Page/Page column 37; 39
[4] Patent: WO2010/135014, 2010, A1. Location in patent: Page/Page column 45-47
[5] Patent: WO2011/87776, 2011, A1. Location in patent: Page/Page column 48; 51