* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Stage #1: With n-butyllithium In tetrahydrofuran at -70℃; for 0.333333 h; Inert atmosphere Stage #2: at -70℃; for 2 h;
Reaction flask was added 0.1mol compound 1-a (reactants), 120ml of tetrahydrofuran (solvent), the sealing installation stirring, nitrogen replacement air, cooled to -70 deg.] C, at a concentration of 0.1mol dropwise 2.5M butyllithium ( reactant) added after 20 minutes, dry carbon dioxide gas is passed through (reactant) to saturation, the reaction at this temperature for 2 hours, the reaction solution was poured into 20ml of concentrated hydrochloric acid has (PH value adjustment) and water 100ml beaker hydrolysis, separated, and extracted with 50ml of ethyl acetate (solvent) aqueous phase was extracted once, and the combined organic phase was washed with brine until neutral, dried over anhydrous sodium sulfate (desiccant) sulfate, and the solvent was concentrated divisible, to give a pale yellow solid of toluene and twice with ethyl acetate twice (solvent) and recrystallized again to give white crystals 3-b, 90percent yield, HPLC purity was 98.0percent.
Reference：
[1] Patent: CN105669595, 2016, A, . Location in patent: Paragraph 0121; 0122; 0123
2
[ 22090-26-2 ]
[ 22090-27-3 ]
Reference：
[1] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1951, p. 166,167, 170[2] Chem.Abstr., 1951, p. 10236
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; for 3h;Reflux;
Reaction flask was added 0.05mol compound 1-a (reactants), 0.06mol4--ethoxy-2,3-difluorophenyl boronic acid (reactant), 0.15mol sodium carbonate (reactants), 100ml of toluene (solvent) , 40ml water (solvent), tetrakistriphenylphosphine palladium 0.1g (catalyst), the reaction mixture was stirred and heated to reflux for 3 hours; cooled to room temperature, separated, the aqueous phase was extracted with 20ml of toluene (solvent), the combined organic phases were washed with water until nature, the solvent was evaporated to dryness, the resultant was dissolved in 80ml petroleum ether (solvent), silica gel column (decoloring agent) decolorized with petroleum ether (solvent) eluate and the solvent was evaporated, the solvent was evaporated to dryness, and the resulting after dissolution with 2 volumes of 2 volumes of toluene and petroleum ether, frozen at -20 recrystallized three times, suction filtered to give a white crystalline product 6-a, yield 80%, purity 99.8% by GC.
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