171032-87-4

基本信息
(S)-1-(2-FLUOROPHENYL)ETHANOL
(S)-2'-Fluorophenylethan-1-ol
(S)-1-(o-Fluorophenyl)ethanol
(S)-1-(2-Ffluorophenyl)ethanol
(1S)-1-(2-Fluorophenyl)ethanol
(1S)-1-(2-Fluorophenyl)ethan-1-ol
(S)-2-Fluoro-alpha-methylbenzyl alcohol
Benzenemethanol,2-fluoro-a-methyl-, (aS)-
Benzenemethanol, 2-fluoro-α-methyl-, (αS)-
物理化學(xué)性質(zhì)
安全數(shù)據(jù)
制備方法

445-27-2

171032-87-4
以鄰氟苯乙酮為原料合成(S)-1-(2-氟苯基)乙醇的一般步驟:在氮?dú)獗Wo(hù)下,將(R)-甲基惡唑硼烷(0.32 g,1.2 mmol)溶于叔丁醇(60 mL)中,加入N,N-二乙基苯胺硼烷(2.6 g,16 mmol),隨后在45℃下緩慢滴加1-(2-氟苯基)乙酮(2.0 g,14 mmol)的叔丁醇溶液(150 mL),攪拌反應(yīng)混合物。反應(yīng)1小時(shí)后,將混合物冷卻至室溫,加入甲醇并濃縮。向濃縮物中加入1.0 N鹽酸,用乙酸乙酯萃取,有機(jī)層依次用飽和食鹽水洗滌和無(wú)水硫酸鈉干燥,濃縮得到粗產(chǎn)物。粗產(chǎn)物通過(guò)硅膠柱色譜純化(洗脫劑:己烷至己烷/乙酸乙酯=85/15),得到標(biāo)題化合物(S)-1-(2-氟苯基)乙醇(1.9 g,收率92%)為無(wú)色液體。1H-NMR(400 MHz,CDCl3)δ:1.52(3H,d,J=6.8 Hz),5.17-5.24(1H,m),6.98-7.05(1H,m),7.15(1H,ddd,J=1.2,7.6,7.6 Hz),7.21-7.28(1H,m),7.49(1H,ddd,J=1.6,7.6,7.6 Hz)。
參考文獻(xiàn):
[1] Journal of the American Chemical Society, 1998, vol. 120, # 51, p. 13529 - 13530
[2] Tetrahedron: Asymmetry, 2003, vol. 14, # 6, p. 710 - 716
[3] Patent: US2018/162868, 2018, A1. Location in patent: Paragraph 1572-1573
[4] Tetrahedron Asymmetry, 2002, vol. 13, # 13, p. 1347 - 1349
[5] Tetrahedron Letters, 2006, vol. 47, # 27, p. 4619 - 4622