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ChemicalBook CAS DataBase List 3-Bromobenzoic acid
585-76-2

3-Bromobenzoic acid synthesis

13synthesis methods
3-Bromobenzoic acid is synthesized from 3-bromotoluene by oxidation of potassium permanganate. Mix m-bromotoluene, potassium hydroxide and water, heat to boiling, slowly add potassium permanganate, and reflux for 4 hours after adding. After acidification by filtration, the crude product was obtained by filtration. Then it is dissolved in ethanol with ammonia water, acidified with hydrochloric acid, filtered and washed with water to obtain 3-bromobenzoic acid.
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Yield:585-76-2 99 %Chromat.

Reaction Conditions:

with water monomer;lithium hydroxide monohydrate in tetrahydrofuran at 25; for 6 h;Reagent/catalyst;

Steps:

General Procedure for Hydrolysis of Esters

General procedure: To a THF (1.0 mL) solution of ester (1.0 mmol) was added a 3.0 mol/L solution of hydroxide (LiOH, NaOH, or KOH) (1.0 mL, 3.0 mmol), and the reaction mixture was stirred at 25 ± 0.02 °C for 0.25-60 h (see Tables 1-4). The reaction was then quenched with 1.0 mol/L HCl (9.0 mL) for 3 min, and the mixture was adjusted accurately to a 250-mL volume with aqueous CH3CN (50% (v/v)). The resulting diluted solution was used for the HPLC an sis as a sample solution with TSkgel ODS-80Ts (150 × 4.6 mm) as a separation column. In the mobile phase, CH3CN/phosphate buffer (1/15 mol/L,pH 7.0) = 1 : 1 (v/v) or CH3CN/H2O (0.1% trifluoroacetic acid(TFA) (v/v)) = 1 : 1 (v/v); flow rate, 1.0 mL/min; measurement at room temperature (20-25 °C); detection wavelength,254 nm. The yield (%) was determined by utilizing the peak area ratios of the reaction mixture to that of the standard acid in the chromatogram.

References:

Hayashi, Kazuhiko;Ichimaru, Yoshimi;Sugiura, Kirara;Maeda, Azusa;Harada, Yumi;Kojima, Yuki;Nakayama, Kanae;Imai, Masanori [Chemical and Pharmaceutical Bulletin,2021,vol. 69,# 6,p. 581 - 594]

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