85-19-8

Usage

Preparation

Preparation by Fries rearrangement of p-chlorophenyl benzoate with aluminium chloride, ? without solvent, at 180° for 10 min (85%), at 155–157° for 2 h (90%), at 130– 140° for 1 h (72%) or at 100–150° for 0.5–3 h (68%) ； ? in refluxing chlorobenzene for 4 h (14%).

InChI:InChI=1/C13H9ClO2/c14-10-6-7-12(15)11(8-10)13(16)9-4-2-1-3-5-9/h1-8,15H

Upstream product

• 2005-08-5 4-chlorophenyl benzoate 
• 623-12-1 4-chloromethoxybenzene 
• 98-88-4 benzoyl chloride 
• 106-48-9 4-chloro-phenol 
• 65-85-0 benzoic acid 
• 117-99-7 2-Hydroxybenzophenone 
• 98-07-7 Benzotrichlorid 
• 94797-02-1 4-Methyl-benzoic acid 2-benzoyl-4-chloro-phenyl ester 
• 591-50-4 iodobenzene 
• 635-93-8 5-chlorosalicyclaldehyde 
• 1483-73-4 diphenyliodonium bromide 
• 71-43-2 benzene 
• 108-86-1 bromobenzene 
• 26965-67-3 4-chloro-2-(hydroxy(phenyl)methyl)phenol 

Downstream Products

• 117-99-7 2-Hydroxybenzophenone 
• 62714-94-7 C₁₇H₁₆ClNO₃ 
• 74271-47-9 chloro-5 hydroxy-2 α-methyl α-phenyl benzene methanol 
• 81393-18-2 Carbamic acid 2-benzoyl-4-chloro-phenyl ester 
• 116544-54-8 (2-Benzoyl-4-chloro-phenoxy)-p-tolyl-acetic acid ethyl ester 
• 125796-51-2 3-benzyl-6-chloro-4-phenylcoumarin 
• 146470-12-4 C₁₄H₁₃ClN₄O*ClH 
• 14098-31-8 6-Chloro-4-phenyl-benzo[e][1,2,3]oxathiazine 2,2-dioxide 
• 94607-36-0 α-phenyl-4-(5'-chloro-2'-hydroxy benzal amino) benzene sulphonamido-2'-thiazole 
• 94593-03-0 α-phenyl-4-(5'-chloro-2'-hydroxy benzal amino) benzene sulphonamido-4',6'-dimethyl-2'-pyrimidine 
• 58430-11-8 (2-benzoyl-4-chlorophenoxy)ethanenitrile 
• 94593-02-9 α-phenyl-4-(5'-chloro-2'-hydroxy benzal amino)benzene sulphonamide 
• 141883-75-2 [5-Chloro-2-(cyclohex-2-enyloxy)-phenyl]-phenyl-methanone 
• 62100-48-5 2-(2-Benzoyl-4-chloro-phenoxy)-2-methyl-propionic acid 

Relevant academic research and scientific papers

Water-Tolerant ortho-Acylation of Phenols

A metal-free, water-tolerant, and one-pot process for ortho-acylation of phenols promoted by the iodine source/hydrogen peroxide system has been developed. This transformation undergoes ether formation, iodocyclization, C-C bond cleavage, and oxidative hydrolysis in a one-step manner, which is supported by control experiments.

Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment?

In this study, we carried out preparative and mechanistic studies on the photochemical reaction of a series of p-substituted phenyl benzoates in confined and sustainable micellar environment. The aim of this work is mainly focused to show whether the nature of the surfactant (ionic or nonionic) leads to noticeable selectivity in the photoproduct formation and whether the electronic effects of the substituents affect the chemical yields and the rate of formation of the 5-substituted-2-hydroxybenzophenone derivatives. Application of the Hammett linear free energy relationship (LFER) on the rate of formation of benzophenone derivatives, on the lower energy band of the UV-visible absorption spectra of the aryl benzoates and 5-substituted-2-hydroxybenzophenone derivatives allows a satisfactory quantification of the substituent effects. Furthermore, UV-visible and 2D-NMR (NOESY) spectroscopies have been employed to measure the binding constant Kb and the location of the aryl benzoates within the hydrophobic core of the micelle. Finally, TD-DFT calculations have been carried out to estimate the energies of the absorption bands of p-substituted phenyl benzoates and 5-substituted-2-hydroxybenzophenone derivatives providing good linear correlation with those values measured experimentally.

Nickel-Catalyzed Decarbonyloxidation of 3-Aryl Benzofuran-2(3H)-ones to 2-Hydroxybenzophenones

We have developed a protocol to facilitate the nickel-catalyzed decarbonyloxidation of 3-aryl benzofuran-2(3H)-ones to 2-hydroxybenzophenones under mild conditions, which is an efficient approach for the decarbonyloxidation of lactones in organic synthesis. A diverse range of substrates can undergo C(O)-O/C(O)-C bond cleavage to generate the target products in good yields. These 2-hydroxybenzophenones can be converted into a variety of compounds via reactions such as esterification, cyclization, and reduction.

Efficient catalytic synthesis method of 2-hydroxybenzophenone compound

The invention discloses a 2-hydroxybenzophenone compound and a green catalytic synthesis method thereof. According to the method, under the conditions of using coumaranone and coumaranone derivativesas raw materials, using nickel chloride as a catalyst, using methylbenzene as a solvent, using di-tert-butyl peroxide as an oxidizing agent, and using sodium carbonate as alkali, the 2-hydroxybenzophenone compound is obtained at high yield. The method has the advantages that the cost is low; the yield is high; the operation is simple and convenient; no pollution is caused and the like. The potential industrial application prospects are realized. The method provides a cheap and green path for the preparation of the 2-hydroxybenzophenone compound.

Practical and efficient synthesis of hydroxyaryl ketones catalyzed by HF@SiO2 under solvent-free condition

A wide variety of hydroxyaryl ketones bearing different motifs was successfully synthesized with good yields and excellent selectivities in the presence of HF@SiO2 as an environmental friendly acid under solvent-free condition. Mild and green reaction conditions and excellent yields (50-91%) make this method an attractive method for the efficient synthesis of hydroxyaryl ketones. Fries rearrangement of phenyl benzoate in the presence of HF@SiO2 led to p-hydroxybenzophenone, while phenyl acetate in the same conditions produced o-hydroxyacetophenone as a single isomer.

Efficient microwave-assisted direct C-benzoylation of phenols and naphthols with benzoic acid catalyzed by bismuth triflate under solvent-free or ionic liquid conditions

An efficient and simple route for the synthesis of ortho-hydroxyaryl ketones has been developed. The microwave-assisted direct C-benzoylation of phenols and naphthols in the presence of metal triflates afforded the corresponding ortho-hydroxyaryl ketones in moderate to excellent yields. Bismuth triflate showed the best catalytic performance compared to other metal triflates. The protocol has advantages including short reaction times, high chemoselectivity towards C-acylation, and simple work-up. Additionally, bismuth triflate can be easily recovered and reused several times without significant loss of catalytic performance.

Series of high spin mononuclear iron(III) complexes with Schiff base ligands derived from 2-hydroxybenzophenones

The reaction of various phenols with benzoyl chloride afforded the derivatives of phenyl benzoate that subsequently underwent Fries rearrangement. The obtained 2-hydroxybenzophenone analogues were combined with linear aliphatic triamines, which afforded pentadentate Schiff base ligands. Moreover, nine new iron(iii) complexes with the general formula [Fe(Ln)X] (where, Ln is the dianion of the pentadentate Schiff base ligand, N,N′-bis((2-hydroxy-5-methylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L1, N,N′-bis((2-hydroxy-3,5-dimethylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L2, N,N′-bis((2-hydroxy-5-chlorophenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L3, N,N′-bis((2-hydroxy-4-methylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L4, N,N′-bis((2-hydroxy-5-bromophenyl)phenyl)methylidene-1,7-diamino-4-azaheptane = H2L5, N,N′-bis((2-hydroxy-5-bromophenyl)phenyl)methylidene-1,7-diamino-4-methyl-4-azaheptane = H2L6 and X is the chlorido, azido or isocyanato terminal ligand) were synthesized and characterized via elemental analysis, and IR and UV-VIS spectroscopy; in addition, the crystal structures of all the complexes were determined by X-ray diffraction. Magnetic investigation reveals high spin state behaviour in all the reported compounds. DFT calculations and analysis of the magnetic functions allowed to extract absolute values of the zero field splitting parameters and exchange coupling constants.

Synthesis and Biological Evaluation of Benzophenone Derivatives as Potential HIV-1 Inhibitors

Background: Although a number of agents can achieve high response in acquired immunodeficiency syndrome (AIDS) patients, safer and more active HIV inhibitors are still needed for the growing number of patients infected with resistant HIV virus strains. GW678248 is one of the most potent benzophenone derivatives, exhibiting high potency against a panel of HIV-1 virus (wild-type, K103N mutant, Y181C, etc.) at 1 nmol/L concentrations. However, the safety issues associated with rash and liver metabolic enzymes ultimately led to discontinue its further deve-lopment. As a continuation of our structural modifications on this template, in this manuscript, a new series of benzophenones are described as potential HIV inhibitors. Methods: All the title molecules were synthesized according to the routes in Scheme 1 and Scheme 2, and were tested for anti-HIV-1 activity using the MTT method. In the molecular simulation, the docking program of AutoDock 4.0.1 in parallel with the default parameters were used. Results: A series of novel benzophenone derivatives (BPs) with nanomolar anti-HIV-1 activity were identified. Of these inhibitors, analogue 10i (EC50 = 2.9 nmol/L), the most active inhibitor, was comparable to the lead compound GW678248 in inhibiting the wild-type HIV-1 virus. Additionally, analogue 13b, which not only exhibited strong inhibitory activity against the HIV-1 virus (EC50 = 4.2 nmol/L), but also has very low cytotoxicity with a TI value of more than 219178.1 was also discovered. Conclusion: This study led to the identification of a series of benzophenone derivatives with nanomolar level of anti-HIV-1 activity. Analogues 10i and 13b, with low cytotoxicity along with high activity are worthy of further development.

Acylation of Csp2-H bond with acyl sources derived from alkynes: Rh-Cu bimetallic catalyzed CC bond cleavage

A Rh-Cu bimetallic catalyzed o-acylation of acyloxacetamide with alkynes has been described. This transformation provides a novel, concise way to synthesize ortho-acylphenols using functionalized alkynes as acylating reagents. Mechanistic studies revealed a Rh-Cu relay process, in which O2 plays a critical role for the formation of carbonyl compounds.

Chemoselective C-benzoylation of phenols by using ALCl3under solvent-free conditions

Substituted phenols were chemo-selectively reacted with benzoylchloride in presence of aluminum chloride under solvent-free condition to afford the corresponding 2′-hydroxy aryl benzophenones in excellent yields (72-96%). Naphthol benzoylation resulted in lower yields as compared to phenols. Both reactions completed in 5-10 min with quantitative yields providing excellent control over regioselectivity of products.