54118-72-8

Usage

Preparation

Obtained by reaction of 4-methoxybenzoyl chloride with thioanisole in the presence of aluminium chloride in carbon disulfide at r.t. for 3 h (37%).

InChI:InChI=1/C15H14O2S/c1-17-13-7-3-11(4-8-13)15(16)12-5-9-14(18-2)10-6-12/h3-10H,1-2H3

Upstream product

• 104-95-0 (4-bromophenyl)thioanisole 
• 100-07-2 4-methoxy-benzoyl chloride 
• 98546-51-1 (4-thiomethoxyphenyl)boronic acid 
• 3446-89-7 4-(Methylthio)benzaldehyde 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1426391-63-0 (p-anisyl)(4-methylthiophenyl)methanol 
• 1426391-10-7 bis[(p-anisyl)(4-methylthiophenyl)methyl] ether 
• 100-68-5 methyl-phenyl-thioether 
• 13205-48-6 4-(methylthio)benzoic acid 
• 100-66-3 methoxybenzene 
• 1442-06-4 4-(methylthio)benzoyl chloride 

Relevant academic research and scientific papers

Base free Suzuki acylation reactions of sodium (aryl trihydroxyborate) salts: A novel synthesis of substituted aryl ketones

The first simple and efficient base free Pd(PPh3)4 catalysed synthesis of substituted aryl ketones from acyl chlorides and easily accessible sodium aryl trihydroxyborate salts in aqueous toluene is reported. The reaction conditions appeared versatile and tolerable to a variety of functional groups including, CF3, OMe, SMe, Br, NO2, F, OH and NH2 furnishing 25 examples of substituted aryl ketones in isolated yields of up to 96% in 24 h. Beside the high purity, the ease and convenience of the isolation compared to boronic acids, sodium aryl trihydroxyborate salts could be used subsequently without the addition of excess amount of an activator and are more user-friendly in terms of the use of accurate reaction stoichiometry.

Palladium-catalyzed cross-coupling of 2-aryl-1,3-dithianes

Palladium-catalyzed cross-coupling of aryl bromides with 2-aryl-1,3-dithianes is described. This methodology takes advantage of the relatively acidic benzylic proton of the dithiane, allowing it to act as a competent, polarity-reversed transmetalation reagent. This unique approach affords the ability to employ an orthogonal deprotection strategy, and practical routes to both diaryl ketones and diarylmethanes are illustrated. Cross-coupling of a range of aryl dithianes with aryl bromides, including scope and current limitations, is presented.

Iodine-catalyzed disproportionation of aryl-substituted ethers under solvent-free reaction conditions

Iodine was demonstrated to be an efficient catalyst for disproportionation of aryl-substituted ethers under solvent-free reaction conditions. Variously substituted 1,1,1′,1′-tetraaryldimethyl ethers were transformed into the corresponding diarylketone and diarylmethane derivatives. I 2-catalyzed transformation of 4-methoxyphenyl substituted ethers yielded mono- and dialkylated Friedel-Crafts products as well. Treatment of trityl alkyl and trityl benzyl ethers with a catalytic amount of iodine produced triphenylmethane and the corresponding aldehydes and ketones. The electron-donating substituents facilitated the reaction, while the electron-withdrawing groups retarded it; the difference in reactivity is not very high. Such an observation may be in favour of hydride transfer, predominantly from the less electron rich side of the ether with more stable carbocation formation. With the isotopic studies it was established that a substantial portion of the C-H bond scission took place in the rate-determining step, while the carbonyl oxygen atom originated from the starting ether, and not from the air. The transformation took place under air and under argon, and HI was not a functioning catalyst.

Catalytic Friedel-Crafts acylation: Magnetic nanopowder CuFe 2O4 as an efficient and magnetically separable catalyst

Catalytic regioselective Friedel-Crafts acylation of an array of anisoles/arenes with various acid chlorides using 5-20 mol % of magnetic nanopowder CuFe2O4 is reported. Unlike the conventional Friedel-Crafts reactions, which are catalyzed by moisture sensitive homogeneous catalysts/promoters, the nanopowder CuFe2O4 catalyst is moisture insensitive and the product/ketone-catalyst isolation is easily achieved using the magnetic properties of CuFe2O4.

MoO2Cl2 as a novel catalyst for Friedel-Crafts acylation and sulfonylation

The use of MoO2Cl2 as a novel catalyst for Friedel-Crafts acylation and sulfonylation is described. A series of aromatic ketones and sulfones were prepared in moderate to good yields using acyl chloride or sulfonyl chloride in the presence of MoO2Cl2 (20 mol %), under solvent-free conditions.

Application of the catalytic friedel-crafts acylation reaction and regioselectivity correlations

A correlation was found between electronic properties and regioselectivity in the Friedel-Crafts reaction of substituted phenylacetic and benzoic acids with anisole, utilising substoichiometric (down to 1 mol%) amounts of catalyst. Relative reactivities of selected catalysts for this reaction were also studied. Georg Thieme Verlag Stuttgart.

Synthesis and structure-activity relationships of benzophenone hydrazone derivatives with insecticidal activity

A broad range of benzophenone hydrazone derivatives was prepared and tested against selected chewing insect pests, allowing the analysis of structure-activity relationships. Good activity was found only when the aromatic rings were substituted at the 4-positions with an halogen atom and a triflate or perhaloalkoxy group. In contrast, a number of substituents on the hydrazone part led to active compounds, the best results being achieved with acyl-type substituents. The excellent laboratory and greenhouse activity of the best representatives was confirmed in semi-field trials against Spodoptera littoralis. ° 2001 Society of Chemical Industry.