66067-44-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Acetylbenzophenone is used as a chemical intermediate for the synthesis of Ketoprofen, a nonsteroidal anti-inflammatory drug (NSAID). It plays a crucial role in the production of Ketoprofen USP Related Compound D, which is utilized for its anti-inflammatory, analgesic, and antipyretic properties to treat various conditions such as pain, fever, and inflammation.
Additionally, 3-Acetylbenzophenone may be employed in the development of other pharmaceutical compounds due to its unique chemical structure and reactivity, potentially leading to the discovery of new drugs with improved efficacy and reduced side effects.

InChI:InChI=1/C15H12O2/c1-11(16)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-10H,1H3

Upstream product

• 22161-82-6 (+)-α-(3-benzylphenyl)propionic acid 
• 22071-15-4 ketoprofen 
• 6304-89-8 3-acetoxybenzoic acid 
• 98-80-6 phenylboronic acid 
• 98-88-4 benzoyl chloride 
• 6343-27-7 1-benzoylpyrrolidine-2,5-dione 
• 22161-82-6 α-(3-benzylphenyl)-propionic acid 
• 55-21-0 benzamide 
• 135364-97-5 tert-butyl benzoyl(tert-butoxycarbonyl)carbamate 
• 65-85-0 benzoic acid 
• 93-99-2 benzoic acid phenyl ester 
• 41908-11-6 3-acetylbenzaldehyde 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 14452-30-3 3'-iodoacetophenone 

Downstream Products

• 56338-25-1 [3-(hydroxymethyl)phenyl](phenyl)methanone 
• 586-42-5 3-acetylbenzoic acid 
• 579-18-0 3-benzoylbenzoic acid 
• 22071-15-4 ketoprofen 

Relevant academic research and scientific papers

Suzuki-Miyaura cross-coupling of esters by selective O-C(O) cleavage mediated by air- And moisture-stable [Pd(NHC)(μ-Cl)Cl]2precatalysts: Catalyst evaluation and mechanism

The cross-coupling of aryl esters has emerged as a powerful platform for the functionalization of otherwise inert acyl C-O bonds in chemical synthesis and catalysis. Herein, we report a combined experimental and computational study on the acyl Suzuki-Miyaura cross-coupling of aryl esters mediated by well-defined, air- and moisture-stable Pd(ii)-NHC precatalysts [Pd(NHC)(μ-Cl)Cl]2. We present a comprehensive evaluation of [Pd(NHC)(μ-Cl)Cl]2 precatalysts and compare them with the present state-of-the-art [(Pd(NHC)allyl] precatalysts bearing allyl-type throw-away ligands. Most importantly, the study reveals [Pd(NHC)(μ-Cl)Cl]2 as the most reactive precatalysts discovered to date in this reactivity manifold. The unique synthetic utility of this unconventional O-C(O) cross-coupling is highlighted in the late-stage functionalization of pharmaceuticals and sequential chemoselective cross-coupling, providing access to valuable ketone products by a catalytic mechanism involving Pd insertion into the aryl ester bond. Furthermore, we present a comprehensive study of the catalytic cycle by DFT methods. Considering the clear advantages of [Pd(NHC)(μ-Cl)Cl]2 precatalysts on several levels, including facile one-pot synthesis, superior atom-economic profile to all other Pd(ii)-NHC catalysts, and versatile reactivity, these should be considered as the 'first-choice' catalysts for all routine applications in ester O-C(O) bond activation.

Water Phase, Room Temperature, Ligand-Free Suzuki–Miyaura Cross-Coupling: A Green Gateway to Aryl Ketones by C–N Bond Cleavage

We report herein a green strategy for synthesis of aryl ketones from twisted amides by using Pd(OAc)2 as catalysts. This method shows high functional group tolerance to offer a variety of ketones in good yields under mild conditions (up to 94 %). Notably, this methodology demonstrates the first water phase, room temperature, ligand-free Suzuki–Miyaura coupling through C–N bond cleavage, which is environmentally friendly and might facilitate the development of amide based green chemistry.

Decarboxylative Oxygenation via Photoredox Catalysis

The direct conversion of aliphatic carboxylic acids to their dehomologated carbonyl analogues has been accomplished through photocatalytic decarboxylative oxygenation. This transformation is applicable to an array of carboxylic acid motifs, producing ketones, aldehydes, and amides in excellent yields. Preliminary results demonstrate that this methodology is further amenable to aldehyde substrates via in situ oxidation to the corresponding acid and subsequent decarboxylative oxygenation. We have exploited this strategy for the sequential oxidative dehomologation of linear aliphatic chains.

FeCl3-catalyzed oxidative decarboxylation of aryl/heteroaryl acetic acids: Preparation of selected API impurities

There is an ever-increasing demand for impurity compounds for use in impurity profiling as regulatory agencies seek information during registration. Herein, we report the FeCl3-catalyzed oxidative decarboxylation of aryl- and heteroaryl acetic acids to the corresponding carbonyl compounds. A variety of useful aldehydes and ketones were prepared in a simple one-pot transformation by employing an environmentally benign, low-cost, and readily available iron salt. The utility of this method has been demonstrated by preparing five valuable API impurities including a multi-gram-scale synthesis of ketorolac impurity B for the first time. This journal is

Photoredox-Catalyzed Decarboxylative Oxidation of Arylacetic Acids

A photoredox-catalyzed decarboxylative oxidation of arylacetic acids, which are privileged scaffolds in pharmaceuticals, is reported herein. The established method is operationally simple and a variety of substrates are applicable, providing rapid access to dehomologated bioisosteres of common pharmaceuticals.

General Method for the Suzuki-Miyaura Cross-Coupling of Primary Amide-Derived Electrophiles Enabled by [Pd(NHC)(cin)Cl] at Room Temperature

A general, highly selective method for the room temperature Suzuki-Miyaura cross-coupling of commonly encountered primary benzamides is reported. A combination of site-selective N,N-di-Boc-activation (tert-butoxycarbonyl activation) of the amide nitrogen with practical air- and moisture-stable, well-defined, and highly reactive [Pd(NHC)(cin)Cl] (NHC = N-heterocyclic carbene; cin = cinnamyl) provides a highly effective route to biaryl ketones from primary amides in high yields. For the first time, a TON of >1000 has been achieved in amide acyl cross-coupling.

N-Acylsuccinimides: Twist-controlled, acyl-transfer reagents in Suzuki-Miyaura cross-coupling by N-C amide bond activation

The palladium-catalyzed Suzuki-Miyaura cross-coupling of N-acylsuccinimides as versatile acyl-transfer reagents via selective amide N-C bond cleavage is reported. The method is user-friendly since it employs commercially-available, air-stable reagents and catalysts. The cross-coupling is enabled by half-twist of the amide bond in N-acylsuccinimides. These highly effective, crystalline acyl-transfer reagents present major advantages over perpendicularly twisted N-acylglutarimides, including low price of the succinimide activating ring, selective metal insertion under redox neutral conditions and high stability of the amide bond towards reaction conditions. Mechanistic studies indicate that oxidative addition is the rate limiting step in this widely applicable protocol.

Preparation process of ketoprofen

The invention discloses a preparation process of ketoprofen. A method takes benzoyl chloride and acetanilide as starting raw materials, and the ketoprofen is prepared through the steps of acylating, carting out acylation, de-protecting, hydrolyzing, carrying out diazotization reduction, carrying out Darzens reaction, oxidizing and the like. According to the method disclosed by the invention, the raw materials have cheap prices and are easy to obtain; the process is easy to realize and a hazardous process does not exist in the reaction; the yield is high and reaction conditions are moderate; the preparation method is simple and convenient to operate and has low requirements on equipment.

Palladium-catalyzed Suzuki-Miyaura coupling of aryl esters

The Suzuki-Miyaura coupling is among the most important C-C bond-forming reactions available due to its reliability, chemoselectivity, and diversity. Aryl halides and pseudohalides such as iodides, bromides, and triflates are traditionally used as the electrophilic coupling partner. The expansion of the reaction scope to nontraditional electrophiles is an ongoing challenge to enable an even greater number of useful products to be made from simple starting materials. Herein, we present how an NHC-based Pd catalyst can enable Suzuki-Miyaura coupling where the C(acyl)-0 bond of aryl esters takes on the role of electrophile, allowing the synthesis of various ketone-containing products. This contrasts known reactions of similar esters that provide biaryls via nickel catalysis. The underlying cause of this mechanistic divergence is investigated by DFT calculations, and the robustness of esters compared to more electrophilic acylative coupling partners is analyzed.

Simple preparation of aryltributylstannanes and its application to one-pot synthesis of diaryl ketones

Transfer of aryl group from boron to tin can be achieved by simple treatment of arylboronic acids with tributyltin methoxide at 100 °C for 1 h under neat conditions. The resulting aryltributylstannanes are applicable to one-pot synthesis of diaryl ketones. Thus, Pd-catalyzed cross-coupling reaction with aroyl chlorides is allowed to proceed without isolation step to produce the corresponding diaryl ketones in good to high yields.