4889-69-4

Usage

Uses

Used in Perfumery:
1(3H)-Isobenzofuranone, 3-(4-chlorophenyl)is used as a fragrance ingredient for its sweet, distinctive scent, contributing to the creation of various perfumes and colognes.
Used in Flavor Industry:
In the flavor industry, 1(3H)-Isobenzofuranone, 3-(4-chlorophenyl)is used as a flavoring agent to impart a unique taste to a range of foods and beverages.
Used in Pharmaceutical Synthesis:
Coumarin is utilized as a precursor in the synthesis of various pharmaceuticals, highlighting its importance in the development of new medications.
Used in Dye Production:
1(3H)-Isobenzofuranone, 3-(4-chlorophenyl)serves as an intermediate in the production of dyes, playing a crucial role in the coloring of different materials.
Used in Anticoagulant Drug Manufacturing:
Coumarin is also used in the manufacturing process of anticoagulant drugs, where it acts as an essential intermediate for the development of these life-saving medications.

Upstream product

• 85-56-3 2-(4-chlorobenzoyl)benzoic acid 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 104-88-1 4-chlorobenzaldehyde 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 593-51-1 methylamine hydrochloride 
• 74-89-5 methylamine 
• 1679-18-1 4-Chlorophenylboronic acid 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 4122-56-9 methyl o-formylbenzoate 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 88070-48-8 N-methylbenzamide 
• 65-85-0 benzoic acid 
• 119-67-5 o-carboxybenzaldehyde 
• 84761-77-3 2-formylphenyl triflate 

Downstream Products

• 1401613-13-5 C₂₈H₃₁ClO₄S 
• 1401613-08-8 2-(4-chlorobenzoyl)phenyl(thiophene-2-yl)methanone 
• 1401613-06-6 C₁₈H₁₁ClOS 

Relevant academic research and scientific papers

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.

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.

Rhenium-Catalyzed Phthalide Synthesis from Benzamides and Aldehydes via C-H Bond Activation

The [4 + 1] annulation of benzamides and aldehydes for phthalide synthesis was achieved via rhenium-catalyzed C-H activation, which demonstrates an unprecedented reaction pattern distinct from those of other transition-metal catalyses. The reaction also features readily available starting materials, a wide scope for both electro-rich and electro-deficient substrates, and the elimination of homoannulation byproducts.

Metal-Free Aerobic Oxidative C–O Coupling of C(sp3)–H with Carboxylic Acids Catalyzed by DDQ and tert-Butyl Nitrite

The formation of the C–O bond is one of the hot topics in the area of C(sp3)–H bond functionalization. A metal-free oxidative cross-coupling between benzylic C(sp3)–H bond and carboxylic acids has been developed. The reactions were performed with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as the catalyst, tert-butyl nitrite (TBN) as the co-catalyst, and molecular oxygen as the terminal oxidant. A variety of diarylmethanes could be successfully coupled with various carboxylic acids to obtain diarylmethanol esters in good to excellent yields. In addition, 2-benzylbenzoic acids could be converted into phthalides in moderate yields through an intramolecular oxidative cyclization.

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.

Rhodium-catalyzed cascade reaction: Aryl addition/intramolecular esterification to access 3-aryl and 3-alkenyl phthalides

Chemical Equation Reprentation First one and then the other: A rhodiumcatalyzed addition of aryl and alkenyl boronic acids to phthalaldehyde and subsequent intramolecular esterification is described (see scheme; cod = l,5-cyclooctadiene, dppb = 1,4-bis(diphenylphosphino)butane). The method is facile and practical for accessing 3-aryl and 3-alkenyl phthalides in moderate to good yields. Several functional groups are tolerated under the reaction conditions.

Palladium-catalyzed cascade aryl addition/intramolecular lactonization of phthalaldehyde to access 3-aryl- and alkenylphthalides

A palladium-catalyzed addition of arylboronic acids to phthalaldehyde, followed by an intramolecular lactonization to access 3-substituted phthalides, is described. The procedure tolerates a series of functional groups, such as methoxyl, fluoro, chloro, and trifluoromethyl groups. It represents a procedure for the synthesis of 3-substituted phthalides.

Cascade synthesis of racemic 3-arylphthalides

Use of the modified reagent system of NaBH4-Amberlyst-15 (H +) for the reduction of o-aroylbenzoates 1a-f followed by simple trituration in aqueous HCl, results in the formation of 3-arylphthalide 3a-f in very short reaction time.