2-(2-bromo-5-methoxyphenyl)ethanol

2-(2-bromo-5-methoxyphenyl)ethanol Property

Boiling point:

314.8±27.0 °C(Predicted)

Density 

1.444±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

14.73±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-(2-bromo-5-methoxyphenyl)ethanol Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 2-(2-bromo-5-methoxyphenyl)ethanol from 2-(3-methoxyphenyl)ethanol: (i) 3-methoxyphenylethanol (1.18 g, 7.8 mmol) and pyridine (0.75 mL, 9.3 mmol) were dissolved in anhydrous dichloromethane (10 mL) under nitrogen protection, stirred and cooled to 0 °C. Subsequently, bromine (0.47 mL, 18.0 mmol) was added slowly and dropwise. The reaction mixture was continued to be stirred at room temperature for 4 h. The solution was orange in color. Upon completion of the reaction, the reaction was quenched by the addition of 10% aqueous sodium bisulfite and extracted with dichloromethane. The organic phases were combined, washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography with gradient elution using hexane and ethyl acetate (10:1, 8:1, 5:1) as eluents to afford the target compound 2-(2-bromo-5-methoxyphenyl)ethanol as a colorless oil (1.5 g, 83.2% yield).1H-NMR (CDCl3) data: δ 7.43 (d, J = 8.8 Hz, 1H) , 6.83 (d, J = 3.3 Hz, 1H), 6.67 (dd, J = 8.8, 3.3 Hz, 1H), 3.91-3.81 (m, 2H), 3.78 (s, 3H), 2.99 (t, J = 6.6 Hz, 2H).

References

[1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 15, p. 7193 - 7205
[2] Patent: EP2963027, 2016, A1. Location in patent: Paragraph 0102; 0103; 0104
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 15, p. 7399 - 7409
[4] Journal of Organic Chemistry, 1981, vol. 46, # 1, p. 118 - 122
[5] Patent: US6239147, 2001, B1