Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 17100-58-2, name is (4-Bromo-2-methylphenyl)methanol. A new synthetic method of this compound is introduced below., Computed Properties of C8H9BrO
Intermediate 16: r2-methvl-4-(4,4.5,5-tetramethyl-1 ,3,2-dioxaborolan-2-vl)phenyllmethanol; A solution of intermediate 15, (4-bromo-2-methylphenyl)methanol, (30 g, 150 mmol), bis(pinacolato)diboron (40 g, 156 mmol), Pd(dppf)CI2(N) (8 g, 10 mmol), and potassium acetate (44 g, 448 mmol) in 1 ,4-dioxane (600 ml.) was heated to reflux under N2 for 4 hours. After cooling, the reaction mixture was filtered, and the filtrate was concentrated in vacuo. Purification by flash chromatography (petroleum ether/ EtOAc: 5/1 ) gave the title compound [2- methyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]methanol as a red oil (34 g, 90%yield). 1H NMR (400 MHz, DMSO-d6) J7.50-7.38 (m, 3H), 5.14 (t, 1 H), 4.51 (d, 2H), 2.22 (s, 3H), 1.28 (s, 12H).
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Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; BOUILLOT, Anne Marie Jeanne; DODIC, Nerina; GELLIBERT, Francoise Jeanne; MIRGUET, Olivier; WO2010/15652; (2010); A2;,
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