Uses
4-bromo-2-methoxyphenol is an important organic intermediate (building block) to synthetize substituted phenzyl products, and it can also be used for the synthesis of polyfunctionalized bicyclic systems.
Uses
It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.
Uses
4-Bromo-2-methoxyphenol is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.A. Schoenberg; R. F. Heck. Palladium-catalyzed formylation of aryl, heterocyclic, and vinylic halides. J. Am. Chem. Soc. 1974, 96 (25), 7761-7764.Joel S. Freundlich; Howard E. Landis. An expeditious aqueous Suzuki-Miyaura method for the arylation of bromophenols. Tetrahedron Letters. 2006, 47(25), 4275-4279.
Synthesis
General procedure for the synthesis of 4-bromo-2-methoxyphenol from guaiacol: NBu4Br3 (1.0 eq.) was dissolved in CH2Cl2 (ca. 5 mL/mmol NBu4Br3), which was immediately added to a CH2Cl2 solution (ca. 5 mL/mmol guaiacol) of guaiacol (1.0 eq.). The reaction mixture was stirred at 23 °C for 2 hours. Subsequently, the solvent was removed under reduced pressure (12 mbar, 40 °C). Water (5.0 mL) was added to the residue and the aqueous layer was extracted with Et2O (3 x 10 mL). The organic layer was separated and dried with MgSO4. The organic solvent was removed under reduced pressure (14 mbar, 40 °C) to give an oily residue, which was finally purified by silica gel column chromatography (SiO2, CH2Cl2).
References
[1] Synthetic Communications, 2007, vol. 37, # 2, p. 323 - 328
[2] Tetrahedron, 2014, vol. 71, # 1, p. 91 - 101
[3] Tetrahedron Letters, 1995, vol. 36, # 10, p. 1705 - 1708
[4] Synlett, 2012, vol. 23, # 7, p. 1082 - 1084
[5] Journal of the Serbian Chemical Society, 2011, vol. 76, # 5, p. 685 - 692
