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ChemicalBook CAS DataBase List 3-BROMOMETHYL-PHTHALIC ACID DIMETHYL ESTER
24129-04-2

3-BROMOMETHYL-PHTHALIC ACID DIMETHYL ESTER synthesis

3synthesis methods
-

Yield:24129-04-2 83%

Reaction Conditions:

with N-Bromosuccinimide in acetonitrile at 70;200W light;

Steps:

5.1.2

A stirred mixture of 3-methyI-phthalic dimethyl ester (12.1 g, 57.9 mmol) and N- bromosuccinimide (12.4 g, 69.5 mmol) in acetonitrile (150 mL) was heated at 700C (oil bath), while a 200W light bulb situated 2 cm away was shining on the reaction mixture overnight. The resulting mixture was cooled and concentrated. The residue was dissolved in ethyl acetate (150 mL), washed with water (3x50 mL) and brine (50 mL), and dried (MgSO4). Solvent was removed in vacuo, and the residue was purified by flash chromatography (SiO2, Hexane:EtOAc 8:2) to give 3- bromomethyl-phthalic dimethyl ester (13.9 g, 83%) as a solid: 1H NMR (CDCl3) δ 7.94-7.90 (dd, J=I .1 and 7.9 Hz, IH), 7.65-7.62 (dd, J=I .0 and 6.9 Hz, I H), 7.47 (t, J=7.8H, IH), 4.54 (s, 2H), 3.97 (s, 3H)1 3.90 (s, 3H).

References:

WO2008/33567,2008,A1 Location in patent:Page/Page column 40-41

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