Molbank 2002, 7, M293

4-Bromo-5-(chloromethyl)-2-methoxyphenol

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]

 

* Author to whom correspondence should be addressed.

 

Received: 20 December 2001 / Accepted: 8 May 2002 / Published: 10 May 2002

 

 

 

2-Bromo-5-hydroxy-4-methoxybenzenemethanol [1] (38.8 g, 166 mmol) in dry chloroform (200 mL) was treated with thionyl chloride (200 mL, 2.76 mol) at 0 °C and stirred for 3 h at ambient temperature. The solvent was removed in vacuo, the residue was dissolved in Et₂O and washed with water (3 x 100 mL), satd. NaHCO₃ (4 x 150 mL) and brine (200 mL), dried over Na₂SO₄, filtered and concentrated in vacuo. The residue was triturated with iPr₂O (2 x 50 mL). Yield: colorless crystals (38.8 g, 93%), mp. 112 - 115 °C.

 

TLC: petroleum ether : EtOAc = 90 : 10, R_f = 0.5.

 

Anal. Calcd for C₈H₈BrClO₂: C, 38.21; H, 3.21. Found: C, 38.46; H, 3.14.

 

¹H NMR (CDCl₃). d 7.05 (s, 1H), 7.00 (s, 1H), 5.65 (s, 1H), 4.60 (s, 2H), 3.85 (s, 3H).

 

¹³C NMR (CDCl₃). d 147.3 (s), 145.2 (s), 129.4 (s), 116.6 (s), 115.1 (d), 113.4 (d), 56.3 (t), 46.2 (q).

 

References and Notes

1. Treu, M. and Jordis, U. MolBank 2002, 7, M278

 

Samples Availability: Available from the authors.

 

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