3-(2-Iodophenyl)propionic acid

Synthesis

Diethyl 2-(2-iodobenzyl)malonate (1.4 g, 3.6 mmol) was added to concentrated HCl (2.3 mL) and water (0.3 mL) and the mixture was refluxed overnight. The progress of the reaction was monitored by TLC and it was confirmed that the feedstock was still unreacted. Concentrated HCl (2 mL) was added additionally and refluxing continued overnight. Upon completion of the reaction, water (20 mL) and ether (50 mL) were added to the mixture for liquid-liquid separation. The organic phase was extracted with 5N ammonium hydroxide solution (30 mL). The basic aqueous phase was slowly added to ice-cold concentrated HCl and a white precipitate was precipitated. The precipitate was collected by filtration, washed with ice water and the solvent was removed in vacuum. 3-(2-iodophenyl)propionic acid was obtained in a yield of 0.32 g and 32%.

References

[1] Journal of Organic Chemistry, 1998, vol. 63, # 20, p. 6859 - 6866
[2] Patent: WO2004/96761, 2004, A1. Location in patent: Page 45