Uses
It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs. It is a medicine intermediate.
Synthesis
1. 1-(4-Bromophenyl)ethanone (9.25 g, 46.5 mmol) was dissolved in tetrahydrofuran (200 mL).
2. The reaction system was cooled at -50 °C in a low temperature bath.
3. An ether solution of methylmagnesium bromide (3 M, 46.5 mL, 139 mmol) was added slowly and dropwise over 15 minutes.
4. After the dropwise addition, the reaction system was allowed to warm gradually to room temperature and stirring was continued for 20 hours.
5. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution.
6. The reaction mixture was extracted with ethyl acetate and the organic phases were combined.
7. The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the crude product as an oil.
8. The crude product was purified by silica gel column chromatography (eluent: 0-20% ethyl acetate/hexane gradient elution) to afford the target product 2-hydroxy-2-(4-bromophenyl)propane (9.1 g, 46.2 mmol, 91% yield). 9. The product was identified by mass spectrometry (MS).
9. The product was characterized by mass spectrometry (ESI): m/z 197.1 [M] , 199.1 [M+2]
References
[1] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3368 - 3383
[2] Patent: WO2010/62571, 2010, A1. Location in patent: Page/Page column 92
[3] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 15, p. 2169 - 2174
[4] Journal of the American Chemical Society, 1971, vol. 93, p. 6877 - 6887
[5] Journal of the American Chemical Society, 1999, vol. 121, # 14, p. 3557 - 3558
