54118-74-0

Usage

Chemical Properties

Solid

Preparation

btained by reaction of 4-methoxybenzoyl chloride with chlorobenzene in the –presence of aluminium chloride in carbon disulfide at r.t. for 3 h (90%).

InChI:InChI=1/C14H11ClO2/c1-17-11-8-6-10(7-9-11)14(16)12-4-2-3-5-13(12)15/h2-9H,1H3

Upstream product

• 5720-07-0 4-methoxyphenylboronic acid 
• 609-65-4 o-chlorobenzoyl chloride 
• 49619-43-4 2-chlorobenzoic anhydride 
• 89-98-5 2-chloro-benzaldehyde 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1174327-78-6 (2-chlorophenyl)(4-methoxyphenyl)methanol 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 53039-46-6 1-chloro-2-(4-methoxybenzyl) benzene 
• 104-93-8 p-methylanizole 
• 100-66-3 methoxybenzene 
• 118-91-2 ortho-chlorobenzoic acid 

Downstream Products

• 1392835-27-6 (R)-(2-chlorophenyl)(4-methoxyphenyl)methanol 
• 55271-06-2 3-(4-methoxyphenyl)-1H-indazole 
• 66938-60-1 (4-Amino-3-nitro-phenyl)-(2-chloro-phenyl)-methanone 
• 55270-71-8 (4-hydroxyphenyl)-(2-chlorophenyl)-methanone 
• 66938-40-7 (2-Chloro-phenyl)-(4-methoxy-3-nitro-phenyl)-methanone 

Relevant academic research and scientific papers

Highly Enantioselective Cobalt-Catalyzed Hydroboration of Diaryl Ketones

A highly enantioselective cobalt-catalyzed hydroboration of diaryl ketones with pinacolborane was developed using chiral imidazole iminopyridine as a ligand to access chiral benzhydrols in good to excellent yields and ee. This protocol could be carried out in a gram scale under mild reaction conditions with good functional group tolerance. Chiral biologically active 3-substituted phthalide and (S)-neobenodine could be easily constructed through asymmetric hydroboration as a key step.

Highly Enantioselective Synthesis of Chiral Benzhydrols via Manganese Catalyzed Asymmetric Hydrogenation of Unsymmetrical Benzophenones Using an Imidazole-Based Chiral PNN Tridentate Ligand

A series of Mn(I) catalysts containing imidazole-based chiral PNN tridentate ligands with controllable "side arm" groups have been established, enabling the asymmetrical hydrogenation of unsymmetrical benzophenones with outstanding activity (up to 13 000 TON) and excellent enantioselectivity (up to >99% ee). This protocol uses K2CO3 as an industrially desirable base and features a wide substrate scope and functional group tolerance. Moreover, the imine group in the catalyst is crucial for accessing high activities and good enantioselectivities.

A kind of alkali to promote self-oxidation of diaryl alkane preparation diarylketones method (by machine translation)

The invention discloses a kind of alkali to promote self-oxidation of diaryl alkane preparation diarylketones method. The method is that the diaryl paraffins compound is dissolved in an organic solvent in the drying of, the addition of a base, in the 25 - 80o C reaction under air or oxygen atmosphere for 0.5 - 5 hours, to obtain diarylketones; said two aryl paraffins compound and alkali molar ratio of 1:1 - 1:3. The method overcomes the need in the prior art strong acid or expensive metal reagent or a strong oxidizing agent and the like, has the following advantages: 1) to oxygen as the oxidizing agent, avoids the use of strong or expensive chemical oxidizing agent; 2) transition metal-free catalyst, avoids the heavy metal ion in the product; 3) the process is simple, low cost, wide range of the substrate, friendly to the environment. The synthesis method disclosed in this invention in the preparation of diarylketones industrialization of the play an important role in the production. (by machine translation)

T-BuONa-Mediated Transition-Metal-Free Autoxidation of Diarylmethanes to Ketones

Autoxidative sp3 C-H transformation of diarylmethanes has been demonstrated using O2-mediation by t-BuONa. This protocol enables an alternative route for the access to diaryl ketones from benzyl derivatives in good to excellent yields under mild reaction conditions, without transition metal catalysts or additional chemical oxidants.

Ni and Cu-catalyzed one pot synthesis of unsymmetrical 1,3-di(hetero)aryl-1: H -indazoles from hydrazine, o -chloro (hetero)benzophenones, and (hetero)aryl bromides

The nickel-catalyzed cyclization of in situ generated ortho-chlorobenzophenone hydrazone derivatives, to afford 3-(hetero)aryl-1H-indazoles, is documented for the first time. The product 1H-indazoles can be transformed subsequently in a one-pot procedure into 1,3-di(hetero)aryl-1H-indazoles via copper-catalyzed N-arylation with (hetero)aryl bromides.

Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes

Highly enantioselective cobalt-catalyzed hydrogenation of 1,1-diarylethenes was developed by using bench-stable chiral oxazoline iminopyridine-cobalt complexes as precatalysts. A unique o-chloride effect was observed to achieve high enantioselectivity. Easy removal as well as further transformations of the chloro group make this protocol a potentially useful alternative to synthesize various chiral 1,1-diarylethanes. This process can be successfully performed under 1 atm of hydrogen at room temperature on gram scale.

Erbium trifluoromethanesulfonate catalyzed Friedel-Crafts acylation using aromatic carboxylic acids as acylating agents under monomode-microwave irradiation

Erbium trifluoromethanesulfonate is found to be a good catalyst for the Friedel-Crafts acylation of arenes containing electron-donating substituents using aromatic carboxylic acids as the acylating agents under microwave irradiation. An effective, rapid and waste-free method allows the preparation of a wide range of aryl ketones in good yields and in short reaction times with minimum amounts of waste.

Chloro-ruthenium complexes with carbonyl and N-(aryl)pyridine-2-aldimines as ancillary ligands. Synthesis, characterization and catalytic application in C-C cross-coupling of arylaldehydes with arylboronic acids

Reaction of N-(aryl)pyridine-2-aldimines (L-R, R = OCH3, CH 3, H, Cl and NO2) with [Ru(CO)2Cl 2]n in refluxing ethanol affords a group of complexes of type [Ru(L-R)(CO)2Cl2]. In these complexes the diimine ligands (L-R) are coordinated to the metal center as NN-donors forming five-membered chelate rings, the carbonyls are mutually cis and the two chlorides are trans. Crystal structure of [Ru(L-OCH3)(CO) 2Cl2] has been determined. All the complexes show characteristic 1H NMR signals, and in dichloromethane solution they display intense absorptions in the visible and ultraviolet regions. Cyclic voltammetry on the complexes shows an irreversible oxidation of the metal center within 1.15-1.23 V vs SCE, and reduction(s) of the diimine ligand within -0.70 to -0.96 V vs SCE. The [Ru(L-R)(CO)2Cl2] complexes efficiently catalyze cross-coupling of arylaldehydes with arylboronic acids yielding diaryl ketones.

CuII-catalyzed asymmetric hydrosilylation of diaryl- and aryl heteroaryl ketones: Application in the enantioselective synthesis of orphenadrine and neobenodine

With certain amounts of sodium tert-butoxide and tert-butanol as additives, catalytic amounts of an inexpensive and easy-to-handle copper source Cu(OAc)2·H2O, a commercially available and air-stable non-racemic dipyridylphosphine ligand, as well as the stoichiometric desirable hydride donor polymethylhydrosiloxane (PMHS), formed a versatile in situ catalyst system for the enantioselective reduction of a broad spectrum of prochiral diaryl and aryl heteroarylketones in air, in high yields and with good to excellent enantioselectivities (up to 96 %). In particular, the practical viability of this process was evinced by its successful applications in the asymmetric synthesis of optically enriched potent antihistaminic drugs orphenadrine and neobenodine. Copyright

Synthesis of arylketones by ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acids

The first ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acids is reported. Various aliphatic and aromatic aldehydes are transformed to the corresponding arylketones. A total of 31 examples with moderate to excellent yields are presented, together with the results of an initial mechanistic investigation.