[Synthesis]
The general procedure for the synthesis of 2-(3-bromophenoxy)acetic acid from methyl 2-(3-bromophenoxy)acetate was as follows: lithium hydroxide monohydrate (8.41 g, 0.2 mol) was slowly added to 100 ml of a water-THF solvent mixture (3:1, v/v) of methyl 2-(3-bromophenoxy)acetate (19.66 g, 80 mmol) at 0 °C. The reaction temperature was maintained at 0 °C and stirring was continued for 15 min. Upon completion of the reaction, the reaction mixture was acidified with aqueous 3N hydrochloric acid to pH < 3. Subsequently, extraction was carried out with ether and the organic phases were combined and dried with anhydrous magnesium sulfate. After filtration to remove the desiccant, the solvent was evaporated under reduced pressure to give 18.21 g of the white solid product 2-(3-bromophenoxy)acetic acid in 98% yield. The melting point of the product was 108 °C. The NMR hydrogen spectrum (200 MHz, CDCl3) data were as follows: δ 4.70 (s, 2H, CH2-O), 6.80-6.90 (m, 1H, ArH), 7.05-7.10 (m, 1H, ArH), 7.15-7.20 (m, 2H, ArH), 9.40-9.05 (br s, 1H, COOH). |