Chemical Properties
yellow to light brown powder
Uses
2-Fluoro-6-iodobenzoic acid may be used for the synthesis of fluoro-substituted benzoyl chlorides. It may be used for the one-pot regioselective synthesis of isocoumarins.
General Description
2-Fluoro-6-iodobenzoic acid is loose white crystal. It can be synthesized by using 2-amino-6-fluorobenzoic acid as the starting material.
Synthesis
At -70°C, n-butyllithium (n-BuLi, 120 mL) was slowly added dropwise to an ether (300 mL) solution of diisopropylamine (33.33 g, 330.00 mmol). The resulting solution was stirred continuously at -70 °C for 1 h. Subsequently, a solution of 1-fluoro-3-iodobenzene (22.2 g, 100.00 mmol) in ether (100 mL) was added. After continued stirring at -70 °C for 1 h, carbon dioxide (CO2, gas) was passed into the reaction mixture. The reaction mixture was stirred at -50°C for 1 hour. After the reaction was completed, the reaction mixture was extracted with deionized water (1 x 300 mL). The pH of the aqueous layer was adjusted to 1 by dropwise addition of 4 M hydrochloric acid (HCl), followed by extraction of the aqueous layer with ethyl acetate (EtOAc, 3 × 300 mL). The organic layers were combined, washed with saturated saline (2 × 100 mL), dried over anhydrous sodium sulfate (Na2SO4), and concentrated to dryness under reduced pressure to afford 8 g (33% yield) of 2-fluoro-6-iodobenzoic acid as a yellow solid.
References
[1] European Journal of Organic Chemistry, 2002, # 19, p. 3351 - 3358
[2] Synthesis, 2005, # 4, p. 617 - 621
[3] Patent: WO2008/103615, 2008, A1. Location in patent: Page/Page column 41
