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2-(2-BROMO-5-METHYL-1,3-THIAZOL-4-YL)ETHANOL synthesis

4synthesis methods
496062-15-8 Synthesis
4-Thiazoleaceticacid,2-bromo-5-methyl-,methylester(9CI)

496062-15-8
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Yield:496062-16-9 74%

Reaction Conditions:

with hydrogenchloride;diisobutylaluminium hydride in dichloromethane;toluene;

Steps:

173 Preparation of 2-(2-bromo-5-methyl-1,3-thiazol-4-yl)ethanol

Example 173 Preparation of 2-(2-bromo-5-methyl-1,3-thiazol-4-yl)ethanol To a solution of ester prepared in Example 172 (3.80 g, 15.2 mmol) in CH2Cl2 (100 mL) was added DIBAL-H (33.4 mL, 33.4 mmol of a 1.0 M solution in toluene) at -78° C. After 15 minutes, the solution was warmed to 0° C. and stirred for an additional 90 minutes. An aqueous solution of 2 N HCl (50 mL) was then added dropwise to quench the excess DIBAL-H. The solvent layers were separated and the aqueous layer extracted with CH2Cl2 (2*200 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (5:2 hexanes/EtOAc) to yield the product (2.5 g, 74%) as a yellowish oil that solidifies upon standing. (C6H8BrNOS) LC-MS, RT 1.38 min., M+H 221.0; 1H NMR (CDCl3): δ 2.31 (s, 3H), 2.82 (t, 2H), 2.90-3.00 (broad s, 1H), 3.89 (t, 2H).

References:

US2003/216391,2003,A1

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