Synthesis
To a stirred solution of 2-(4-iodophenyl)acetic acid (2.00 g, 7.63 mmol) in tetrahydrofuran (150 mL) was slowly added borane-tetrahydrofuran complex (1.0 M solution of tetrahydrofuran, 7.63 mL, 7.63 mmol) at room temperature. The reaction mixture was stirred continuously for 6 hours at room temperature. Upon completion of the reaction, the reaction mixture was diluted with saturated sodium chloride solution and the pH was adjusted with aqueous sodium hydroxide solution to 13. Subsequently, extraction was carried out with ethyl acetate and the organic phases were combined and dried over anhydrous sodium sulfate. After filtration to remove the desiccant, the filtrate was concentrated under reduced pressure to give 4-iodophenylethanol (620 mg, 33% yield) as a light orange solid. The product could be used in subsequent reactions without further purification. The results of low resolution mass spectrometry (electrospray ionization, ESI) were as follows: calculated value (C8H9IO) 248.1; measured value 271.1 (M + Na)+.
References
[1] Angewandte Chemie - International Edition, 2011, vol. 50, # 34, p. 7865 - 7869
[2] Journal of the American Chemical Society, 2001, vol. 123, # 9, p. 1828 - 1833
[3] Liebigs Annalen der Chemie, 1994, # 11, p. 1075 - 1092
[4] Patent: WO2006/102760, 2006, A1. Location in patent: Page/Page column 121
[5] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 5, p. 647 - 652
