In order to control the quality of crisaborole(1)and its tablets,six related substances were synthesized based on the synthetic process of 1,namely 3-(4-cyanophenoxy)benzyl acetate(related substance A),4,4'-di(4-cyanophenoxy)-2,2'-bis(acetoxymethyl)biphenyl(related substance B),4,4'-di(4-cyanophenoxy)-2,2'-bis(hydroxymethyl)-biphenyl(related substance C),4-[4-[4-bromo-3-(hydroxymethyl)phenoxy]-3-(hydroxymethyl)phenoxy]benzonitrile(related substance D),5-[2-(acetoxymethyl)-4-(4-cyanophenoxy)phenoxy]-2-bromobenzyl acetate(related substance E)and 4-[(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-5-yl)oxy]benzoic acid(related substance F).Their structures were confirmed by 1H NMR,13C NMR and MS,and the purities of all impurities were greater than 97％.
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