23405-31-4

Usage

InChI:InChI=1/C11H10O4/c1-2-14-10(12)7-3-4-9-8(5-7)6-15-11(9)13/h3-5H,2,6H2,1H3

Upstream product

• 227954-90-7 (1-oxo-1,3-dihydroisobenzofuran-5-yl)carbonyl chloride 
• 96259-69-7 diethyl 2-(bromomethyl)terephthalate 
• 65399-05-5 5-amino-3H-isobenzofuran-1-one 
• 4792-29-4 5-carboxyphtalide 
• 85118-25-8 1-oxo-1,3-dihydroisobenzofuran-5-carboxamide 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 50-00-0 formaldehyd 
• 64-17-5 ethanol 
• 64169-34-2 5-bromophthalide 
• 95-92-1 oxalic acid diethyl ester 
• 4383-39-5 Propiolsaeure-(2-propinyl)ester 
• 623-47-2 propynoic acid ethyl ester 
• 1255217-89-0 ethyl 1,3-dihydroisobenzofuran-5-carboxylate 
• 82104-74-3 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile 

Downstream Products

• 85118-25-8 1-oxo-1,3-dihydroisobenzofuran-5-carboxamide 

Relevant academic research and scientific papers

Synthesis of phthalides from bis-propargyl ethers: Use of Garratt-Braverman cyclization to construct the phthalans and IBX as a new reagent for subsequent oxidation

An efficient route to phthalides is described starting from easily available bis-propargyl ethers. The method involves Garratt-Braverman cyclization of the ethers to phthalans which are then efficiently oxidized to the phthalides by iodoxy benzoic acid (IBX) which has been shown to be a superior reagent in terms of yield and reagent stoichiometry for such a transformation in comparison with more commonly used KMnO4/CuSO4 reagent.

Synthesis of Isobenzofuranones by Cobalt Catalyzed [2+2+2] Cycloaddition

Highly regioselective cobalt catalyzed [2+2+2] cycloaddition of diynes and monoynes to afford isobenzofuranones in good yields is described. The reaction proceeds in the presence of cheap and readily available cobalt catalyst with a sterically hindered pyridine-2,6-diimine ligand. Applicability of the method can also be extended to the synthesis of isoindolinones.

Diethyloxalate as “CO” Source for Palladium-Catalyzed Ethoxycarbonylation of Bromo- and Chloroarene Derivatives

Palladium(II)-catalyzed ethoxycarbonylation of aryl bromides with diethyloxalate oxalate is described. Functionalized aromatic esters can be efficiently synthesized with only 0.65 mol % PdCl2(PPh3)2 catalyst under microwav

INTERMEDIATES FOR THE PREPARATION OF CITALOPRAM AND ESCITALOPRAM

Methods for manufacture of 5-alkoxycarbonylphthtalides are disclosed. The 5-alkoxycarbonylphthtalides are useful in syntheses of the well-known antidepresssants citalopram and escitalopram.

Method for the preparation of 5-cyanophthalide

A method for the preparation of 5-cyanophthalide in which 5-carboxyphthalide is converted to the corresponding amide of Formula (IV) in which R is hydrogen or C1-6 alkyl, which is then reacted with a dehydrating agent thereby obtaining 5-cyanophthalide. The conversion of 5-carboxyphthalide to the corresponding amide of Formula (IV) may be carried out via the corresponding C1-6 alkyl or phenyl ester or the acid chloride, which is converted to the amide of Formula (IV) by amidation with ammonia or a C1-6 alkylamine. By the process 5-cyanophthalide, an important intermediate used in the preparation of the antidepressant citalopram, is prepared in high yields by a convenient, cost effective procedure.

Substituent Effects on Hydrogenation of Aromatic Rings: Hydrogenation vs. Hydrogenolysis in Cyclic Analogues of Benzyl Ethers.

Carbalkoxy substituents are shown to retard the hydrogenation of aromatic rings over Rh/C catalyst.Hydrogenolysis predominates with acyclic (benzyloxy)acetates over this catalyst, but both hydrogenation and hydrogenolysis become sluggish with 2-isochroman-4-ones (1).However, phthalides may be cleanly hydrogenated in moderate to excellent yields without significant hydrogenolysis.Placing a benzyl ether in a ring system appears to greatly retard hydrogenolysis relative to the acyclic analogues.