Methyl 2-(broMoMethyl)-5-cyanobenzoate synthesis
- Product Name:Methyl 2-(broMoMethyl)-5-cyanobenzoate
- CAS Number:421551-82-8
- Molecular formula:C10H8BrNO2
- Molecular Weight:254.08
103261-68-3
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421551-82-8
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Yield:421551-82-8 90%
Reaction Conditions:
with N-Bromosuccinimide;dibenzoyl peroxide in tetrachloromethane at 80; for 12 h;
Steps:
IV: To a solution of methyl 5-cyano-2-methyl-benzoate III (61 .0 g, 348 mmol, 1 .00 eq) and N-bromosuccinimide (75.8 g, 383 mmol, 1 .10 eq) in carbon tetrachloride (650 mL) was added benzoyl peroxide (8.43 g, 34.8 mmol, 0.100 eq). The mixture was stirred at 80 °Cfor 1 2 h. The mixture was concentrated in vacuum, suspended in water (500 mL) and then extracted with ethyl acetate (2 x 500 mL). The aqueous phase was extracted with ethyl acetate (2 x 300 mL). The combined organic phase was washed with brine (2 x 100 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate = 0/1 to 5/1 ) to afford methyl 2-(bromomethyl)-5-cyano- benzoate IV (80.0 g, 31 5 mmol, 90% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3-d) δ = 8.20 (d, J = 1 .6 Hz, 1 H), 7.70 (dd, J = 1 .8, 8.0 Hz, 1 H), 7.54 (d, J = 8.0 Hz, 1 H), 4.89 (s, 2H), 3.91 (s, 3H).
References:
WO2021/69705,2021,A1 Location in patent:Page/Page column 115-116
79669-50-4
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42872-79-7
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39478-78-9
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60710-80-7
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