4-Methoxy-2-nitrobenzyl bromide Chemical Properties

Melting point:

66.5℃ (ethanol )

Density 

1.589±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

2-8°C

Appearance

Light yellow to yellow Solid

Safety Information

HS Code 

2916399090

4-Methoxy-2-nitrobenzyl bromide Usage And Synthesis

Synthesis

General procedure for the synthesis of 1-(bromomethyl)-4-methoxy-2-nitrobenzene from 4-methyl-3-nitroanisole: Intermediate 1: Synthesis of 1-(bromomethyl)-4-methoxy-2-nitrobenzene: To a solution of 4-methyl-3-nitroanisole (16.53 mL, 119.64 mmol, 1 eq.) in carbon tetrachloride (500 mL), N-bromosuccinimide (21.29 g, 119.64 mmol, 1 eq.) and azobisisobutyronitrile (392.9 mg , 2.39 mmol, 0.02 equiv). The reaction mixture was heated to reflux at 85 °C for 20 hours. After completion of the reaction, the solution was cooled to room temperature and filtered to remove the resulting succinimide precipitate. The filtrate was concentrated to give a yellow oil. The oily substance was allowed to crystallize overnight at -25°C. It was subsequently dissolved in ethyl acetate (15 mL), petroleum ether was added and allowed to stand at -25°C for 2 hours to promote recrystallization. The crystallized product was washed with petroleum ether and dried under vacuum to give 17.4 g (59% yield) of 1-(bromomethyl)-4-methoxy-2-nitrobenzene as a liquid. Product Characterization: 1H NMR (DMSO-d6) δ 7.68 (d, J = 8 Hz, 1H), 7.56 (d, J = 3 Hz, 1H), 7.33 (dd, J = 8.0, 3.0 Hz, 1H), 4.89 (s, 2H), 3.87 (s, 3H). HPLC (max plot) 99%; Rt 4.09 min.

References

[1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 261 - 269
[2] Journal of Organic Chemistry, 1984, vol. 49, # 7, p. 1238 - 1246
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 9, p. 3231 - 3244
[4] Journal of Organic Chemistry, 2003, vol. 68, # 23, p. 9100 - 9104
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6048 - 6057

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