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ChemicalBook CAS DataBase List 5-Bromosalicylic acid

5-Bromosalicylic acid synthesis

13synthesis methods
-

Yield:89-55-4 95%

Reaction Conditions:

with tetrapropylammonium nonabromide in dichloromethane at 23; for 0.5 h;Inert atmosphere;

Steps:

Brominations with Pr4NBr9; General Procedure A
General procedure: A round-bottom flask equipped with a magnetic stir bar and a rubber septum was charged with Pr4NBr9 (0.66 mmol, 0.33 mol%) and CH2Cl2 (1 mL). The homogeneous solution was stirred and cooled to 0 °C if not described otherwise (partial precipitation of the nonabromide can occur at this point). The substrate (2.0 mmol, 1.0equiv) was added and the reaction allowed to warm to 23 °C (attention: exothermic reaction) After the reported reaction time the dark-red color of the nonabromide had vanished and TLC control showed completion of the reaction. The reaction was quenched by addition of sat. aq Na2S2O3 (2 mL) and transferred to a separation funnel. H2O was added (15 mL) followed by extraction with Et2O (4 × 20 mL) if not described otherwise. The organic layers were combined, washed with H2O (4 × 15 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to give the crude product.

References:

Beck, Thorsten M.;Haller, Heike;Streuff, Jan;Riedel, Sebastian [Synthesis,2014,vol. 46,# 6,art. no. SS-2013-Z0693-FA,p. 740 - 747]

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