2-Bromo-4-methoxy-5-(1-methylethoxy)benzeneacetic Acid Ethyl Ester

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: 27 February 2003

2-Bromo-4-methoxy-5-(1-methylethoxy)benzeneacetic acid chloride [1] (3.00 g, 9.33 mmol) was treated with dry EtOH (50 mL) at 0 °C. The solution was stirred at ambient temperature for 1 h and then evaporated in vacuo. The residue was partitioned between Et₂O (50 mL) and satd. NaHCO₃ (50 mL), the organic layer was washed with satd. NaHCO₃ (3 x 50 mL) and brine (1 x 50 mL), dried over Na₂SO₄, filtered and evaporated in vacuo. The crude product was triturated with cold iPr2O (2 x 10 mL). Yield: colorless crystals (2.93 g, 95%); mp. 48 - 49 °C.

TLC: petroleum ether : EtOAc = 80 : 20, R_f = 0.6.

Anal. Calcd for C₁₄H₁₉BrO₄: C, 50.77; H, 5.78. Found: C, 50.82; H, 5.67.

¹H NMR (CDCl₃): d 7.00 (s, 1H), 6.80 (s, 1H), 4.44 (Septett, J = 6.4 Hz, 1H), 4.14 (q, J = 6.8 Hz, 2H), 3.78 (s, 3H), 3.63 (s, 2H), 1.31 (d, J = 6.4 Hz, 6H), 1.25 (t, J = 6.8 Hz, 3H).

¹³C NMR (CDCl₃): d 170.6 (s), 150.1 (s), 146.4 (s), 125.9 (s), 118.4 (d), 116.0 (d), 115.2 (s), 71.7 (d), 60.7 (t), 56.0 (q), 40.9 (t), 21.8 (q), 14.0 (q).

References and Notes

1. Treu, M.; Jordis, U. Molbank 2002, M295.

Samples Availability: Available from the authors.

© 2002 MDPI. All rights reserved.