Boron tribromide → Ethyl 2-(4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate

Beteiligte Stoffe

Reaktionsschritte

To a −80° C. solution of 2-(4-methoxy-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (550 mg, 2 mmol) in dichloromethane (20 mL) is added BBr3 (5 mL, 1M solution in dichloromethane). The reaction is stirred at ambient temperature overnight. The reaction is quenched by addition of methanol and is concentrated in vacuo. The residue is partitioned between EtOAc and 1N HCl. The organic layer is concentrated and the residue is purified by chromatography (0 to 30% EtOAc in hexanes) to give the title compound as a tan solid, (500 mg, 95%). LC-ES/MS m/e 264 (M+1), 1H NMR (DMSO-d6) δ 10.22 (s, 1H), 7.82 (d, 2H), 6.86 (d, 2H), 4.27 (q, 2H), 2.64 (s, 3H), 1.29 (t, 3H).

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