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ChemicalBook CAS DataBase List 5-BROMO-2-ETHOXYBENZOIC ACID
60783-90-6

5-BROMO-2-ETHOXYBENZOIC ACID synthesis

3synthesis methods
-

Yield:60783-90-6 89%

Reaction Conditions:

with bromine;acetic acid at 25;

Steps:

5-bromo-2-ethoxy-benzoic acid (26)

To a solution of commercially available 2-ethoxybenzoic acid (25) (50 g, 0.3 mol) in AcOH (500 mL) was added Br2 (72 g, 0.45 mol) slowly at room temperature and the mixture was stirred at room temperature overnight. Then, after LC-MS showed the starting material was consumed completely, aqueous Na2SO3 was added and the mixture was concentrated. The residue was extracted with EtOAc and the organic layer was washed with aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered and concentrated to give compound 26 (65.41 g, 89%) as a white solid. ESI-MS m/z 245.0 [M+H]+ calc. for C9H9BrO3. This intermediate was used in the next step without further purification or characterization.

References:

Rabal, Obdulia;Sánchez-Arias, Juan A.;Cuadrado-Tejedor, Mar;de Miguel, Irene;Pérez-González, Marta;García-Barroso, Carolina;Ugarte, Ana;Estella-Hermoso de Mendoza, Ander;Sáez, Elena;Espelosin, Maria;Ursua, Susana;Haizhong, Tan;Wei, Wu;Musheng, Xu;Garcia-Osta, Ana;Oyarzabal, Julen [European Journal of Medicinal Chemistry,2018,vol. 150,p. 506 - 524] Location in patent:supporting information

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