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ChemicalBook CAS DataBase List 4-BROMO-3,5-DIMETHYL-BENZOIC ACID METHYL ESTER

4-BROMO-3,5-DIMETHYL-BENZOIC ACID METHYL ESTER synthesis

4synthesis methods
-

Yield: 84%

Reaction Conditions:

Stage #1:methanol;4-bromo-3,5-dimethylbenzaldehyde with potassium iodide at 50;
Stage #2: with tert.-butylhydroperoxide in methanol for 24 h;Reflux;

Steps:

Compound 3.
To a 250 mL flask was added compound 2 (4.0 g,19 mmol), MeOH (100 mL) and KI (623 mg, 3.8 mmol). The mixturewas stirred at 50 °C before t-BuOOH (3.9 mL, 70% (aq), 28 mmol) wasadded dropwise over 30 min. Then the mixture was refluxed for 24 h.After cooling to room temperature, saturated Na2S2O3 (aq) was added.The mixture was extracted with ethyl acetate, dried over anhydrousNa2SO4 and evaporated in vacuo. The residue was purified by columnchromatography on silica gel with petroleum ether/ethyl acetate (15:1,v/v) to afford compound 3 as a white solid (3.8 g, 84%). 1H NMR(400 MHz, CDCl3) δ 7.73 (s, 2H), 3.90 (s, 3H), 2.46 (s, 6H).

References:

Song, Heli;Tang, Weiqiang;Zhao, Shuangliang;Liu, Qingyun;Xie, Yongshu [Dyes and Pigments,2018,vol. 155,p. 323 - 331]

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