main applications of pyridine 4-toluenesulfonate_kain industrial additives

background and overview^[1]

pyridine 4-methylbenzenesulfonate can be used as a pharmaceutical synthesis intermediate.

apply^[1-3]

pyridine 4-methylbenzenesulfonate can be used as a pharmaceutical synthesis intermediate. examples of its application are as follows:

1) prepare 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde. this method first prepares 3-bromo-4-[(3-fluorobenzyl)oxy ] benzaldehyde and pyridinium 4-methylbenzenesulfonate, and then react 3-bromo-4-[(3-fluorobenzyl)oxy]benzaldehyde with pyridinium-4-methylbenzenesulfonate to form 2- (3-bromo-4-((3-fluorobenzyl)oxy)phenyl)-1,3-dioxolane, followed by 2-(3-bromo-4-((3-fluorobenzyl) oxy)phenyl)-1,3-dioxolane is hydroxylated to obtain 2-((3-fluorobenzyl)oxy)-5-formylphenylboronic acid, and finally 2-((3-fluorobenzyl) )oxy)-5-formylphenylboronic acid is coupled with m-fluorobenzyl bromide to obtain the target product. the invention provides a method for directly preparing 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde. the 3-(3-fluorobenzyl)-4-( the yield of 3-fluorobenzyloxy)benzaldehyde is as high as 64.85%, and the purity measured by high performance liquid chromatography reaches 98.92%.

2) used to prepare the new compound 2-(3-bromo-4-(3-fluorobenzyloxy)phenyl)-1,3-dioxolane and its preparation method. this method first prepares 3 -bromo-4-(3-fluorobenzyloxy)benzaldehyde with pyridinium 4-methylbenzenesulfonate, then 3-bromo-4-(3-fluorobenzyloxy)benzaldehyde with 4-methylbenzene pyridinium sulfonate reacts to form 2-(3-bromo-4-(3-fluorobenzyloxy)phenyl)-1,3-dioxolane. the new compound 2-(3-bromo-4-(3-fluorobenzyloxy)phenyl)-1,3-dioxolane provided by the invention can be used to directly prepare 3-(3-fluorobenzyl)- 4-(3-fluorobenzyloxy)benzaldehyde, and the yield of the prepared 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde is as high as 64.85%, measured by high performance liquid chromatography the purity reaches 98.92%.

3) used to prepare a new compound 2-(3-fluorobenzyloxy)-5-formylphenylboronic acid. this method first prepares 3-bromo-4-[(3-fluorobenzyl)oxy base] benzaldehyde (formula 3) and pyridinium 4-methylbenzenesulfonate (formula 6), and then compound 3 reacts with compound 6 to generate 2-(3-bromo-4-(3-fluorobenzyloxy)phenyl )-1,3-dioxolane (formula 7), compound 7 undergoes coupling reaction to obtain 2-(3-fluorobenzyloxy)-5-formylphenylboronic acid (formula 8). the new compound 2-(3-fluorobenzyloxy)-5-formylphenylboronic acid provided by the invention can be used to prepare 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde, and the yield of prepared 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde reaches 64.85%, and the purity measured by high performance liquid chromatography reaches at least 98.92%.

main reference materials

[1] preparation method of cn201610711939.83-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde

[2] cn201610711679.42-(3-bromo-4-(3-fluorobenzyloxy)phenyl)-1,3-dioxolane and preparation method thereof

[3] cn201610715421.12-(3-fluorobenzyloxy)-5-formylphenylboronic acid and preparation method thereof