7472-96-0

Upstream product

• 86911-84-4 4-Hydroxy-4-(2-methoxy-phenyl)-but-2-ynoic acid ethyl ester 
• 1165952-91-9 cyclohexa-1,3-diene 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 135-02-4 ortho-anisaldehyde 
• 4122-56-9 methyl o-formylbenzoate 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 7468-67-9 o-formylbenzonitrile 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 84761-77-3 2-formylphenyl triflate 
• 119-67-5 o-carboxybenzaldehyde 
• 119-36-8 methyl salicylate 
• 57271-91-7 N-butyl-2-hydroxybenzamide 

Downstream Products

• 1151-04-8 2-(2-methoxybenzoyl)benzoic acid 

Relevant academic research and scientific papers

Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy- N-Butylbenzamides

The N-butyl amide group, CONHBu, has been found to be an effective promoter of the [1,2]-Wittig rearrangement of aryl benzyl ethers and thus allow the two-step synthesis of isomerically pure substituted diarylmethanols starting from simple hydroxybenzoic acid derivatives. The method is compatible with a wide range of functional groups including methyl, methoxy, and fluoro, although not with nitro and, unexpectedly, is applicable to meta as well as ortho and para isomeric series.

Efficient One-Pot Synthesis of 3-Substituted Phthalides via Additive Arylation of Organozinc Intermediate

In recent years, substitution at the third position on phthalides has been proven a valua-ble synthetic intermediate for developing active molecules. We reported a direct and efficient one-pot method for the synthesis of 3-aryl Phthalides performed by adding organo-zinc reagent on methyl-2-formylbenzoate; reagent formed in-situ by the reaction between diethylzinc and different aryl boronic acid derivatives without using any ligand. The possible mechanism involved a coordi-nated zinc carbonyl transition state, arylation, and followed by the intramolecular cyclization. The substituents groups in boronic having different electronic and steric properties played an important role in the reaction completion time and yield. The structure elucidation and confirmation of the synthesized compounds were done by using H-NMR analytical data. The method can be useful for synthesizing various scaffolds and intermediates in search of potentially active compounds.

Direct and selective synthesis of 3-arylphthalides via nickel-catalyzed aryl addition/intramolecular esterification

Herein we report a nickel-catalyzed aryl addition/intramolecular esterification in a cascade fashion. Under the combination of commercially available nickel precursor and tridentate ligand, the one pot protocol offers a direct, simple and regioselective approach to access 3-aryl phthalide derivatives from two readily available substrates with good efficiency, broad scope as well as satisfactory functional group compatibility.

Catalytic asymmetric synthesis of 3-aryl phthalides enabled by arylation-lactonization of 2-formylbenzoates

The catalytic asymmetric synthesis of 3-aryl phthalides is reported through a sequential asymmetric arylation-lactonization reaction. The reaction is enabled by a boron-zinc exchange to generate reactive arylating agents, which react with 2-formylbenzoates in the presence of a chiral amino naphthol ligand. The enantiodetermining step is the arylation of the aldehyde, which then undergoes a lactonization event to yield the corresponding phthalides in good yields and enantioselectivities.

Rhodium or palladium-catalyzed cascade aryl addition/intramolecular lactonization of phthalaldehydonitrile to access 3-aryl and 3-alkenyl phthalides

A rhodium or palladium-catalyzed addition of boronic acids to phthalaldehydonitrile, followed by an intramolecular lactonization of cyano to access 3-substituted phthalides, is described. This procedure tolerates a series of functional groups, such as methoxy, fluoro, chloro, and vinyl groups. It is a novel procedure for the synthesis of 3-arylphthalides.

Rhodium or palladium-catalyzed cascade aryl addition/ intramolecular lactonization of phthalaldehyde with potassium organotrifluoroborates to access 3-arylphthalides

An efficient rhodium-catalyzed lactonization of phthalaldehyde with potassium organotrifluoroborates to access 3-arylphthalides has been developed. Moreover, palladium is a also good catalyst for such transformation.

Transition metal-catalyzed addition reactions of arylboronic acids with alkyl 2-formylbenzoates: Efficient access to chiral 3-substituted phthalides

Transition metal-catalyzed addition of arylboronic acids to 2-formylbenzoates afforded 3-substituted phthalides. By using SPINOL-based phosphites as ligands, a Rh(i)-catalyzed asymmetric version of such an addition reaction was achieved. The Royal Society of Chemistry 2010.

Synthesis of phthalide derivatives using nickel-catalyzed cyclization of o-haloesters with aldehydes

The reaction of o-bromobenzoate (1b) with benzaldehyde (2a) in the presence of [NiBr2(dppe)] (dppe = 1,2-bis(diphenylphosphino)ethane) and zinc powder in THF (24 hours, reflux temperature), afforded 3-phenyl-3H- isobenzofuran-1-one (3a) in an 86% yield. Similarly, o-iodobenzoate reacts with 2a to give 3a, but in a lower yield (50%). A series of substituted aromatic and aliphatic aldehydes (2b, 4-MeC6H4CHO; 2c, 4-MeOC 6H4CHO; 2d, 3-MeOC6H4-CHO 2e, 2-MeOC6H4-CHO; 2f, 4-CNC6H4CHO; 2g, 4-(Me)3-CC6H4CHO; 2h, 4-C6H 4C6H4CHO; 2i, 4-ClC6H 4CHO; 2j, 4-CF3C6H4CHO; 2k, CH 3(CH2)5CHO; 21, CH3(CH 2)2-CHO) also underwent cyclization with o-bromobenzoate (1b) producing the corresponding phthalide derivatives in moderate to excellent yields and with high chemoselectivity. Like 1b, methyl 2-bromo-4,5- dimethoxybenzoate (1c) reacts with tolualdehyde (2b) to give the corresponding substituted phthalide 3m in a 71% yield. The methodology can be further applied to the synthesis of six-membered lactones. The reaction of methyl 2-(2-bromophenyl)acetate (1d) with benzaldehyde under similar reaction conditions afforded six-membered lactone 3o in a 68% yield. A possible catalytic mechanism for this cyclization is also proposed.