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ChemicalBook CAS DataBase List 4-BROMO-2-METHYLTHIAZOLE
298694-30-1

4-BROMO-2-METHYLTHIAZOLE synthesis

3synthesis methods
-

Yield:298694-30-1 55%

Reaction Conditions:

Stage #1:2,4-dibromo-1,3-thiazole with n-butyllithium in tetrahydrofuran;hexanes at -78; for 1 h;
Stage #2:dimethylsulfite in tetrahydrofuran;hexanes at -78 - 20;

Steps:

52
Example 52; 4-Bromo-2-methyl-thiazole (142); 2,4-Dibromothiazole (2.4 g, 9.8 mmol) was dissolved in abs. THF (50 ml) and the resulting solution was stirred under argon at -78 °C. A solution of BuLi (4.2 ml, 6 mmol, 2.5 M in hexanes) was added and the stirring was continued for Ih whereafter a solution of dimethylsulfate (2.7 ml) in THF (5 ml) was added dropwise. After stirring for 4h at -78 °C, the reaction mixture was warmed to room temperature and stirred EPO overnight. The reaction mixture was diluted with saturated aqueous sodium bicarbonate (50 ml). The aqueous layer was extracted into diethyl ether and the combined organic extracts were washed with brine dried with magnesium sulfate and concentrated by rotary evaporation. Purification by column chromatography on silica gel gave the title compound as yellow oil (0.956 g, 55%).

References:

TIBOTEC PHARMACEUTICALS LTD.;MEDIVIR AB WO2007/14922, 2007, A1 Location in patent:Page/Page column 121-122

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