ChemicalBook CAS DataBase List 1,3-Benzenedicarboxylic acid, 2-broMo-, 1,3-diMethyl ester

1,3-Benzenedicarboxylic acid, 2-broMo-, 1,3-diMethyl ester synthesis

7synthesis methods

Product Name:1,3-Benzenedicarboxylic acid, 2-broMo-, 1,3-diMethyl ester
CAS Number:39622-80-5
Molecular formula:C10H9BrO4
Molecular Weight:273.08

22433-91-6 Synthesis

22433-91-6
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1,3-Benzenedicarboxylic acid, 2-broMo-, 1,3-diMethyl ester

39622-80-5
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Yield: 94%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 20; for 24 h;Inert atmosphere;

Steps:

17 Synthesis of Dimethyl 2-bromobenzene-l,3-dicarboxylate (26)
[00211] To a stirring solution of 2-bromobenzene-l,3-dicarboxylic acid (25.15 g, 102.64 mmol) in anhydrous DMF (250 mL) at ambient temperature under nitrogen was added anhydrous K2CO3 (31.5 g, 227.92 mmol), followed by iodomethane (32.376 g, 14.2 mL, 228.10 mmol). The reaction mixture was stirred at this temperature for 24 h. The reaction mixture was poured into brine (750 mL), and the product was extracted with ethyl acetate (3 x 250 mL). The combined organic layers were washed with brine (450 mL), dried over anhydrous sodium sulfate and concentrated to afford dimethyl 2- bromobenzene-l,3-dicarboxylate (28.45 g, 94%) as an amber oil. The product was carried to the next step without further purification. NMR (250 MHz, DMSO-dr,) d 7.91 - 7.74 (m, 2H), 7.70 - 7.52 (m, 1H), 3.88 (s, 6H). ESI-MS m/z calc. 271.9684, found 273.4 (M+l)⁺; Retention time: 4.23 minutes (LC Method C).

References:

VERTEX PHARMACEUTICALS INCORPORATED;ABELA, Alexander Russell;ABRAHAM, Sunny;ANDERSON, Corey Don;ARUMUGAM, Vijayalaksmi;CHAU, Jaclyn;CLEMENS, Jeremy;CLEVELAND, Thomas;DWIGHT, Timothy A.;FRIEMAN, Bryan A.;HADIDA RUAH, Sara Sabina;ISHIHARA, Yoshihiro;KRENITSKY, Paul;MCCARTNEY, Jason;MELILLO, Vito;MILLER, Mark Thomas;SILINA, Alina;UY, Johnny;ZHOU, Jinglan WO2020/206080, 2020, A1 Location in patent:Paragraph 00211

67-56-1 Synthesis