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ChemicalBook CAS DataBase List Methyl 2-(bromomethyl)acrylate

Methyl 2-(bromomethyl)acrylate synthesis

6synthesis methods
-

Yield:4224-69-5 89%

Reaction Conditions:

with N-Bromosuccinimide;sodium chloride in diethyl ether;dichloromethane

Steps:

Preparation of Methyl 2-bromomethyl-2-propenoate
Preparation of Methyl 2-bromomethyl-2-propenoate To a solution of N-bromosuccinimide (5.17 g, 26.8 mmoles) in dry dichloromethane (40 ml) were added dimethyl sulphide (4 ml) in dichloromethane (50 ml), drop by drop with stirring at 0° C. for 10 min. To the resulting mixture was added methyl 3-hydroxy-2-metylidene-propanoate (3.15 g, 31.50 mmoles) dissolved in dichloromethane (40 ml), leaving it for 24 hours at room temperature. At the end of that time, it was poured into an aqueous solution of sodium chloride and ice. An extraction was performed with diethyl ether (3*100 ml), and the result was washed with water and dried over anhydrous sodium sulphate. Following vacuum concentration, 4.33 g of a yellow oil was obtained (89% yield) of methyl 2-bromomethyl-2-propenoate.

References:

Barrera, Jaime Bermejo;Silva, Margarita Hernandez;De Mon, Melchor Alvarez;Ranieri, Juan Pablo Pivel US2003/199575, 2003, A1

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