methyl 5-(bromomethyl)isoxazole-3-carboxylate synthesis

Yield: 51%

Reaction Conditions:

with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in tetrachloromethaneReflux;

Steps:

1 Synthesis of C103-6
To a solution of C103-5 (7.05 g, 50 mmol) in CC (250 mL), was added NBS (11.5 g, 65 mmol) and AIBN (820 mg, 5 mmol). The reaction mixture was heated under reflux overnight. After being cooled to room temperature, the reaction mixture was poured into water; the aqueous layer was extracted with DCM twice. The combined layer was washed with saturated NaHC0₃, dried over Na₂S0₄, filtered and concentrated in vacuo. The residual oil was purified by flash chromatography on silica gel to give C103-6 (5.56 g, yield: 51%). MS (ESI) m/z: 221 [M+H]⁺.

References:

CENTRAX INTERNATIONAL, INC.;YANG, Jinfu;CEN, Jian James;FAN, Xiaoqing Michelle WO2016/11088, 2016, A2 Location in patent:Paragraph 0097; 0098