[4-(2-Bromoethyl)phenoxy]-(1,1-dimethylethyl)dimethylsilane

Matthias Treu and Ulrich Jordis*

Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163OC, A-1060 Vienna, Austria

Tel. +43 (1) 58801.15460, Fax +43(1)58801.15499, Email: [email protected]

Received: 20 December 2001 / Accepted: 8 May 2002 / Published: 24 February 2003

To 4-(2-bromoethyl)phenol [1] (28.75 g, 143 mmol) and tert-butyldimethylchlorosilane (23.64 g, 159 mmol) in dry THF (600 mL), imidazole (24.27 g, 357 mmol) was added at 15 °C over 10 min and stirred at ambient temperature. The mixture was filtered, the filtrate was concentrated in vacuo, and the residue was dissolved in Et₂O (300 mL), washed with dil. AcOH (pH 5.5, 2 x 300 mL), water (2 x 300 mL), satd. NaHCO₃ (1 x 250 mL), dried over Na₂SO₄, filtered and concentrated in vacuo. The residue was purified by column chromatography (250 g SiO₂, petroleum ether : EtOAc = 95 : 5). Yield: colorless oil (32.92 g, 73%).

TLC: petroleum ether : EtOAc = 2 : 1, R_f = 0.95.

Anal. Calcd for C₁₄H₂₃BrOSi: C, 53.33; H, 7.35. Found: C, 53.56; H, 7.35.

¹H NMR (CDCl₃): d 7.10 (d, J = 8.0 Hz, 2H), 6.81 (d, J = 8.0 Hz, 2H), 3.53 (t, J = 6.7 Hz, 2H), 3.11 (t, J = 6.7 Hz, 2H), 1.04 (s, 9H), 0.22 (s, 6H).

¹³C NMR (CDCl₃): d 154.5 (s), 131.6 (s), 129.5 (d), 120.1 (d), 38.7 (t), 33.1 (t), 25.6 (q), 18.1 (s), - 4.5 (q).

References and Notes

1. Torssell, K.; Wahlberg, K. Isolation, structure, and synthesis of alkaloids from Valeriana officinalis. Acta Chem. Scand. 1967, 21, 53-62.

Samples Availability: Available from the authors.

© 2002 MDPI. All rights reserved.