110706-48-4

Upstream product

• 75990-95-3 2-methylhydrogen-3-chlorophthalate 
• 117-21-5 3-chlorophthalic anhydride 
• 89-20-3 4-chlorophthalic acid 
• 27563-65-1 3-chlorobenzene-1,2-dicarboxylic acid 
• 75990-94-2 1-methyl hydrogen-3-chlorophthalate 
• 608-23-1 3-chloro-o-xylene 
• 61539-35-3 3-chlorophthalic acid dimethyl ester 
• 70097-45-9 7-chloroisobenzofuran-1(3H)-one 
• 52010-22-7 4-chloroisobenzofuran-1(3H)-one 

Downstream Products

• 22479-40-9 1,2-bis(bromomethyl)-6-chlorobenzene 
• 452978-99-3 [2-(([tert-butyl(dimethyl)silyl]oxy)methyl)-6-chlorophenyl]methanol 

Relevant academic research and scientific papers

Synthesis of 1,2-phenylenedimethanols by base-promoted reduction of isobenzofuran-1(3H)-ones with silane

An efficient method for preparation of substituted 1,2-phenylenedimethanols and aliphatic 1,4-diols that are valuable intermediates in organic synthesis, has been developed by the base-promoted reduction of isobenzofuran-1(3H)-ones and γ-lactones with silane under mild conditions. Compared with traditional procedures using stoichiometric amounts of metal hydrides and alkyl reductants, the present method avoids the use of sensitive reagents and is operationally simple and a broad variety of functional groups are tolerated.

Assessment of the regioselectivity in the condensation reaction of unsymmetrical o-phthaldialdehydes with alanine

One approach for the synthesis of isoindolinones, a privileged bioactive heterocyclic core structure, involves a condensation reaction of o-phthaldialdehydes with a suitable nitrogen-containing nucleophile. This fascinating reaction is revisited here in the context of the use of o-phthaldialdehydes that contain additional substituents in the aromatic ring leading to a detailed analysis of the regioselectivity of the reaction. Eleven monosubstituted o-phthaldialdehydes were synthesised and reacted with alanine. The regioselectivity observed across the eleven substrates led to the design of a disubstituted substrate that reacted with very high control. A gram-scale reaction followed by esterification gave one major regioisomer in high yield. In addition, the regioselectivity observed on reaction of two novel monodeuterated substrates led to an increased mechanistic understanding.

Selective lithiation of 4- and 5-halophthalans

The reaction of 4- and 5-halophthalans 5 with lithium and a catalytic amount of DTBB at -78 °C leads to the formation of the corresponding functionalized organolithium intermediates 6 and 11, which by reaction with carbonyl compounds give, after hydrolysis, the expected substituted phthalans 8 and 13, respectively. When after reaction with the carbonyl compound the system is allowed to react at 0 °C, a second lithiation occur: A reductive opening of the heterocycle takes place with some regioselectivity leading to new organolithium intermediates 9 and 14/15 that by reaction with electrophiles lead, after hydrolysis, to polyfunctionalized molecules 10 and 16/17, respectively.

Isoindolin-1-one glucokinase activators

Isoindolin-1-one-substituted propionamide glucokinase activators which increase insulin secretion in the treatment of type II diabetes.

2-[2H-(1,3-dihydroisoindole)alkylene]-4,5-dihydroimidazoles and pharmaceutical compositions thereof

A compound of formula (I): STR1 or a pharmaceutically acceptable salt, ester or amide thereof, wherein: Z represents a residue of a substituted or unsubstituted aryl group, X represents O or NRo wherein Ro represents a hydrogen atom,

On the regioselectivity of metal hydride reductions of 3-substituted phthalic anhydrides

A problem of 3-methoxyphthalide reduction by metal hydrides was reinvestigated. Various effects controlling selectivity of reductions in 3-substituted phthalides were studied, and a qualitative interpretation of the results is now proposed. Methods for obtaining enhanced yields of one or the other lactonic product were developed.