1-(chloromethyl)-4,5-dimethoxy-2-nitrobenzene synthesis
- Product Name:1-(chloromethyl)-4,5-dimethoxy-2-nitrobenzene
- CAS Number:15862-94-9
- Molecular formula:C9H10ClNO4
- Molecular Weight:231.63
1016-58-6
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Yield:15862-94-9 98%
Reaction Conditions:
with thionyl chloride;triethylamine in dichloromethane at 0 - 20; for 12 h;
Steps:
b 1-(Chloromethyl)-4,5-dimethoxy-2-nitrobenzene (1)
Step (b):
To a solution of (4,5-dimethoxy-2-nitrophenyl)methanol (19.5 g, 91 mmol) in CH2Cl2 (55 mL) was added a few drops of triethylamine, and SOCl2 (1.3 mL, 18 mmol) at 0 °C.
After stirring overnight at room temperature, the reaction was quenched by addition of EtOH.
The organic layer was washed with water and brine, dried over Na2SO4, filtered off and concentrated under reduced pressure.
After purification by column chromatography on silica gel (Cyclohexane/EtOAc 7:3), the pure product 1 (20.7 g, 90 mmol) was obtained as a yellow solid.
Yield, 98%. m.p: 59.9 °C. 1H NMR (250 MHz, CDCl3) δ 7.68 (s, 1H), 7.09 (s, 1H), 5.00 (s, 2H), 4.00 (s, 3H), 3.96 (s, 3H).
13C NMR (100 MHz, CDCl3) δ 153.5, 148.8, 140.4, 127.3, 112.9, 108.5, 56.6, 56.5, 43.7.
References:
Da Costa, Laurène;Roche, Manon;Scheers, Els;Coluccia, Antonio;Neyts, Johan;Terme, Thierry;Leyssen, Pieter;Silvestri, Romano;Vanelle, Patrice [European Journal of Medicinal Chemistry,2016,vol. 115,p. 453 - 462]
20357-25-9
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121-33-5
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120-14-9
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7306-46-9
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