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

Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163OC, A-1060 Vienna, Austria
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Molbank 2002, 2002(1), M293; https://doi.org/10.3390/m293
Submission received: 20 December 2001 / Accepted: 8 May 2002 / Published: 10 May 2002
Graphical Abstract
Molbank 2002 m293 i001
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, Rf = 0.5.
Anal. Calcd for C8H8BrClO2: C, 38.21; H, 3.21. Found: C, 38.46; H, 3.14.
1H NMR (CDCl3). δ 7.05 (s, 1H), 7.00 (s, 1H), 5.65 (s, 1H), 4.60 (s, 2H), 3.85 (s, 3H).
13C NMR (CDCl3). δ 147.3 (s), 145.2 (s), 129.4 (s), 116.6 (s), 115.1 (d), 113.4 (d), 56.3 (t), 46.2 (q).

Supplementary Material

References and Notes

  1. Treu, M.; Jordis, U. MolBank 2002, 7, M278.
Sample Availability: Available from the authors.

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MDPI and ACS Style

Treu, M.; Jordis, U. 4-Bromo-5-(chloromethyl)-2-methoxyphenol. Molbank 2002, 2002, M293. https://doi.org/10.3390/m293

AMA Style

Treu M, Jordis U. 4-Bromo-5-(chloromethyl)-2-methoxyphenol. Molbank. 2002; 2002(1):M293. https://doi.org/10.3390/m293

Chicago/Turabian Style

Treu, Matthias, and Ulrich Jordis. 2002. "4-Bromo-5-(chloromethyl)-2-methoxyphenol" Molbank 2002, no. 1: M293. https://doi.org/10.3390/m293

APA Style

Treu, M., & Jordis, U. (2002). 4-Bromo-5-(chloromethyl)-2-methoxyphenol. Molbank, 2002(1), M293. https://doi.org/10.3390/m293

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