5-Bromovanillin synthesis
- Product Name:5-Bromovanillin
- CAS Number:2973-76-4
- Molecular formula:C8H7BrO3
- Molecular Weight:231.04
121-33-5
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2973-76-4
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Yield:2973-76-4 99%
Reaction Conditions:
with bromine in methanol at 0 - 25; for 1 h;
Steps:
3-Bromo-4-hydroxy-5-methoxybenzaldehyde (5-bromovanillin) (9) [1].
To a stirred, cooled (0-5 °C) solution of 4-hydroxy-3-methoxybenzaldehyde - vanillin 8 (70.03 g, 460.26 mmol) in methanol (500 ml) bromine (80.94 g, 506.35 mmol) was added during 30 min. The mixture was then stirred at room temperature for 30 min and poured into ice-cold water (1500 ml). Resulting solid was collected by filtration, washed with water and dried in vacuo to give 9 as pale yellow crystals. Yield 99% (105.88 g, 458.28 mmol). mp 164-166°C (lit. [1] mp 163- 164 °C). Rf (EtOAc/n-hexane, 3:1) 0.50.
References:
Stefański, Tomasz;Mikstacka, Renata;Kurczab, Rafa?;Dutkiewicz, Zbigniew;Kucińska, Ma?gorzata;Murias, Marek;Zielińska-Przyjemska, Ma?gorzata;Cichocki, Micha?;Teubert, Anna;Kaczmarek, Mariusz;Hogendorf, Adam;Sobiak, Stanis?aw [European Journal of Medicinal Chemistry,2018,vol. 144,p. 797 - 816] Location in patent:supporting information
71119-08-9
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108-20-3
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121-33-5
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