Methyl 5-Benzyloxy-4-Methoxy-2-nitrobenzoate synthesis
- Product Name:Methyl 5-Benzyloxy-4-Methoxy-2-nitrobenzoate
- CAS Number:164161-49-3
- Molecular formula:C16H15NO6
- Molecular Weight:317.29
215659-03-3
100-39-0
164161-49-3
The reaction was carried out with methyl 5-hydroxy-4-methoxy-2-nitrobenzoate (15.4 g, 68 mmol) and benzyl bromide (9.7 mL, 82 mmol) in the presence of cesium carbonate (44 g, 136 mmol) with stirring at room temperature in DMSO (200 mL) for 24 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (~2 L) and n-butanol (~100 mL). The organic layer was washed sequentially with water and brine, dried with magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (eluent ratio from 1:5 to 2:1 ethyl acetate-hexane) to afford methyl 2-nitro-4-methoxy-5-benzyloxybenzoate 20.2 g in 94% yield; MS (AP/CI): 286.1 (M + H)+.
215659-03-3
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Yield: 97%
Reaction Conditions:
with potassium carbonate in acetonitrile at 80; for 4 h;
Steps:
2 Step 2
Methyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate A solution of the product from the previous step (5.3 g, 23 mmol), (bromomethyl)benzene (6.0 g, 35 mmol) and K2CO3(6.3 g, 46 mmol) in MeCN (100 mL) was stirred at 80 °C for 4 h. The solvent was removed, the residue taken up in water, and the product extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to give the title compound as a yellow solid (7 g, 97%). MS (ES+) C16H15NO6 requires: 317, found: 318[M+H]+.
References:
BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM;HEYMACH, John;ROBICHAUX, Jacqulyne;NILSSON, Monique;JONES, Philip;CROSS, Jason;THEROFF, Jay WO2020/219904, 2020, A1 Location in patent:Paragraph 0474
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