Yield:762287-57-0 73%

Reaction Conditions:

Stage #1:2-bromo-5-chloroanisole with n-butyllithium in tetrahydrofuran at -78; for 0.666667 h;Inert atmosphere;
Stage #2:Trimethyl borate in tetrahydrofuran at 20; for 3 h;Inert atmosphere;

Steps:

1 Synthesis of Intermediate I-1
Synthesis of Intermediate I-1 10262] 22.1 g (100 mmol) of 2-bromo-5-chioroanisole was dissolved in 500 ml of THF, and stirred in a N2 atmosphere at-78° C. for 10 minutes. Then, 44 mL of 2.5 M n-BuLi was slowly added thereto by using a dropping funnel, and the mixture was additionally stirred for 30 minutes. 10.4 g (110 mmol) of trimethyl borate was slowly and dropwisely added thereto by using a dropping flannel, and the mixture was additionally stirred for 3 hours at room temperature. Next, an organic layer was extracted therefrom once by using 300 ml of 1 M HC1 and three times by using water and diethylether. The organic layer was dried using magnesium sulfate, and a solvent was removed thereform by evaporation. The residue was separated and purified through a silica gel chromatography to obtain 13.61 g of Intermediate 1-1 (73 mmol, yield:73%). The compound thus obtained was confirmed by usingMS/FAB.10263] C7H8BC103 Cal. 186.40. Found. 186.47.

References:

SAMSUNG DISPLAY CO., LTD.;KIM, Sooyon;KIM, Kwanghyun;KIM, Youngkook;HAN, Sanghyun;HWANG, Seokhwan US2016/190448, 2016, A1 Location in patent:Paragraph 0261; 0262; 0263

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