Chemical Properties
clear colorless liquid
Uses
3-Bromophenethyl alcohol may be used as a starting material in the synthesis of its mesylate derivative (
m-Br-C
6H
4CH
2CH
2OMs) by treatment with mesyl chloride.
General Description
3-Bromophenethyl alcohol is a phenethyl alcohol derivative. Its enthalpy of vaporization at boiling point has been determined.
Synthesis
The general procedure for the synthesis of 3-bromophenylethanol using 3-bromophenylacetic acid as starting material was as follows: to a solution of 3-bromophenylacetic acid (2.00 g, 9.3 mmol) was slowly added BH3-Me2S (7 mL of a 2M THF solution, 14.0 mmol) at 0 °C. The reaction mixture was gradually warmed up to room temperature with continuous stirring for 20 hours. Upon completion of the reaction, the mixture was again cooled to 0 °C and water (10 mL) was added dropwise to quench the reaction. Subsequently, the organic layer was separated, washed with brine (20 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a colorless oily crude product. Purification by column chromatography (eluent: 50% EtOAc in heptane solution) resulted in 3-bromophenethyl alcohol as a colorless oil (1.47 g, 79% yield). The product was detected by mass spectrometry showing m/z 224/226 [M + H]+, and the 1H NMR (300 MHz, CDCl3) data were as follows: δ 7.41-7.35 (2H, m), 7.23-7.16 (2H, m), 3.87 (2H, t, J = 6.5 Hz), 2.86 (2H, t, J = 6.5 Hz).
References
[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3018 - 3022
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2007, vol. 50, # 3, p. 183 - 188
[3] Patent: WO2008/53136, 2008, A1. Location in patent: Page/Page column 38
[4] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2882 - 2891
[5] Journal of Medicinal Chemistry, 1998, vol. 41, # 3, p. 358 - 378
