Synthesis
a) Synthesis of 3-iodophenyl acetate
3-Iodophenol (3 g, 13.6 mmol), acetyl chloride (2.9 ml, 40.9 mmol) and potassium carbonate (9.42 g, 68.2 mmol) were dissolved in N,N-dimethylformamide (75 ml) and the reaction was stirred for 16 hours at room temperature. After completion of the reaction, the mixture was partitioned between water and ethyl acetate. The organic layer was washed with 1N NaOH solution, dried over anhydrous magnesium sulfate and subsequently concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 20% ethyl acetate/hexane as eluent to give 2.3 g (65% yield) of 3-iodophenyl acetate. Nuclear magnetic resonance hydrogen spectroscopy (1H NMR, CDCl3) data were as follows: δ 7.57 (1H, m), 7.46 (1H, m), 7.08 (2H, m), 2.29 (3H, s).
References
[1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2079 - 2098
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 4, p. 926 - 934
[3] Journal of Medicinal Chemistry, 1997, vol. 40, # 23, p. 3804 - 3819
[4] Patent: US2003/18064, 2003, A1
[5] Patent: WO2012/49460, 2012, A1. Location in patent: Page/Page column 43
