55191-20-3

Usage

Uses

Fenofibric Acid intermediate.

Preparation

Preparation by Fries rearrangement of o-chlorophenyl benzoate with aluminium chloride without solvent for 2 h at 152–155° (88%) or at 160°.

Upstream product

• 10547-61-2 (3-chloro-4-methoxyphenyl)(phenyl)methanone 
• 95-57-8 2-monochlorophenol 
• 98-88-4 benzoyl chloride 
• 766-51-8 2-Chloroanisole 
• 6284-79-3 3,4-dichlorobenzophenone 
• 54683-91-9 o-chlorophenyl benzoate 
• 695-99-8 2-Chloro-1,4-benzoquinone 
• 536-74-3 phenylacetylene 
• 98-07-7 Benzotrichlorid 
• 1137-42-4 4-Hydroxybenzophenone 

Downstream Products

• 179018-56-5 [3-chloro-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-phenyl-methanone 
• 3704-69-6 1-[3-Chlor-4-(2-dimethylamino-1-methyl-aethoxy)-phenyl]-2-(4-chlor-phenyl)-1-phenyl-aethanol 
• 179019-00-2 [3-chloro-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-phenyl-methanol 
• 3950-36-5 3-Chlor-4-<2-dimethylamino-1-methyl-aethoxy>-benzophenon 

Relevant academic research and scientific papers

Visible Light-Mediated [2 + 2] Cycloaddition Reactions of 1,4-Quinones and Terminal Alkynes

A single-step synthesis of 4-hydroxy-functionalized bi-aryl and aryl/alkyl ketones via oxidative coupling of terminal alkynes with benzoquinones is reported. Furthermore, with naphthoquinones, owing to the cross-resonance of carbonyl with the aromatic ring, alkene-alkyne cycloaddition is more favored to give four-membered carbocyclic adducts, thereby precluding the requirement of preactivated alkynes.

Preparation of hydroxybenzophenones using silica-gel supported ferric chloride

The synthesis of commercially important hydroxybenzophenones by condensing phenols with benzotrichloride has been reported. Benzoylation is catalyzed by silica supported ferric chloride under solvent-free conditions. Hydroxybenzophenones are isolated in low to moderate yields.

LTA4 Hydrolase inhibitors

The present invention provides compounds of the formula Ar1-Q-Ar2-Y-R-Z and pharmaceutically acceptable salts thereof wherein Ar1 and Ar2 are optionally substituted aryl moieties, Z is an optionally substituted nitrogen-containing moiety which may be an acyclic, cyclic or bicyclic amine or an optionally substituted monocyclic or bicyclic nitrogen-containing heteroaromatic moiety; Q is a linking group capable of linking two aryl groups; R is an alkylene moiety; Y is a linking moiety capable of linking an aryl group to an alkylene moiety and wherein Z is bonded to R through a nitrogen atom. The compounds and pharmaceutical compositions of the present invention are useful in the treatment of inflammatory diseases which are mediated by LTB4 production, such as proriasis, ulcerative colitis, IBD and asthma.

Fries rearrangement in ionic melts

1-Butyl-3-methylimidazolium chloroaluminate, [BMIm]+Al2Cl7-, was used as a solvent as well as a Lewis acid catalyst in Fries rearrangement reactions of phenyl benzoates. The rate of consumption of phenyl benzoate obeyed first-order kinetics. Good yields and high selectivity are the features observed in this unconventional but interesting aprotic solvent.

Structure-activity relationship studies on 1-[2-(4- phenylphenoxy)ethyl]pyrrolidine (SC-22716), a potent inhibitor of leukotriene A4 (LTA4) hydrolase

Leukotriene B4 (LTB4) is a pro-inflammatory mediator that has been implicated in the pathogenesis of a number of diseases including inflammatory bowel disease (IBD) and psoriasis. Since the action of LTA4 hydrolase is the rate-limiting step for LTB4 production, this enzyme represents an attractive pharmacological target for the suppression of LTB4 production. From an in- house screening program, SC-22716 (1, 1-[2-(4- phenylphenoxy)ethyl]pyrrolidine) was identified as a potent inhibitor of LTA4 hydrolase. Structure-activity relationship (SAR) studies around this structural class resulted in the identification of a number of novel, potent inhibitors of LTA4 hydrolase, several of which demonstrated good oral activity in a mouse ex vivo whole blood assay.

Alumina in Methanesulfonic Acid (AMA) as a New Efficient Reagent for Direct Acylation of Phenol Derivatives and Fries Rearrangement. A Convenient Synthesis of o-Hydroxyarylketones

Alumina in methanesulfonic acid (AMA) is used to prepare o-hydroxyaryl ketones by acylation of phenol and naphthol derivatives with carboxylic acids and the Fries rearrangement of phenolic esters. Mechanistic studies show that the acylation reaction in AMA occurred through an esterification followed by a Fries rearrangement of the phenolic ester by an intermolecular mechanism.

Substituted aminoalkoxybenzene anti-fungicidal compositions and use

The compound of the formula STR1 wherein each of R1 and R2 individually is hydrogen, lower alkyl or lower alkenyl or together signify straight-chain alkylene with 2 to 4 carbon atoms, R3 is hydrogen, halogen or lower alkyl, Q is alkylene with 4 to 11 carbon atoms and at least 4 carbon atoms between the two free valencies or alkenylene with 4 to 11 carbon atoms and at least 4 carbon atoms between the two free valencies and each of Y and Y' individually is a direct bond or the group --CH2 --, --CH2 CH2 --, --CH=CH-- or --C C--, the group R1 R2 N--Q--O-- is attached to the 3- or 4 -position of ring A and the symbol R designates that the ring to which it is attached is unsubstituted or is substituted with at least one substitutent selected from the group consisting of halogen, trifluoromethyl, cyano, nitro, lower alkyl and lower alkoxy, and their pharmaceutically acceptable acid addition salts can be used for the control or prevention of fungal infections, especially of topical or systemic infections which are caused by pathogenic fungi, and for the manufacture of antifungally-active medicaments. The compounds of formula I have not only a pronounced antifungal activity, but they also exhibit synergistic effects in combination with other known antifungally-active substances which inhibit sterol biosynthesis such as ketoconazole and terbinafine.

A convenient synthesis of 2-nitrophenols from 1,2-dichlorobenzenes

Aromatic nucleophilic substitution of 1,2-dichlorobenzenes 1 possessing a strong electron-withdrawing group in the 4-position with a nitrite ion give the corresponding 2-nitrophenols 5.