35509-94-5

Upstream product

• 587-03-1 3-methylbenzyl alcohol 
• 620-19-9 1-chloromethyl-3-methyl-benzene 
• 7145-06-4 diethyl (3-methylbenzyl) phosphate 
• 108-38-3 m-xylene 
• 131403-60-6 3-methylbenzyl trimethylsilyl ether 

Downstream Products

• 2348-47-2 3-methylbenzyl radical 
• 502610-56-2 diethyl 2-acetyl-2-(3-methylbenzyl)succinate 
• 1358991-65-7 C₂₃H₂₆O₄ 
• 710967-01-4 C₁₄H₁₅NS 
• 38612-03-2 3-methylbenzyl benzoate 
• 6315-20-4 2-(3-methylbenzyl)succinic acid 
• 4168-10-9 2-(3-methylbenzyl)succinic anhydride 

Relevant academic research and scientific papers

Aliphatic C-H Bond Iodination by a N-Iodoamide and Isolation of an Elusive N-Amidyl Radical

Contrary to C-H chlorination and bromination, the direct iodination of alkanes represents a great challenge. We reveal a new N-iodoamide that is capable of a direct and efficient C-H bond iodination of various cyclic and acyclic alkanes providing iodoalkanes in good yields. This is the first use of N-iodoamide for C-H bond iodination. The method also works well for benzylic C-H bonds, thereby constituting the missing version of the Wohl-Ziegler iodination reaction. Mechanistic details were elucidated by DFT computations, and the N-centered radical derived from the used N-iodoamide, which is the key intermediate in this process, was matrix-isolated in a solid argon matrix and characterized by UV-vis as well as IR spectroscopy.

Iminophosphorane-mediated regioselective umpolung alkylation reaction of α-iminoesters

Umpolung reactions of imines, especially the asymmetric reactions, have been extensively studied as they provide access to important chiral amines in an efficient manner. The reactions studied range from simple Michael reactions to several kinds of other reactions such as the aza-benzoin reaction, aza-Stetter reaction, addition with MBH carbonate, and Ir-catalysed allylation. Herein, we report the first umpolung alkylation reaction of α-iminoesters with alkyl halides mediated by iminophosphorane as an organic superbase. The desired products were obtained in up to 82% yield with almost perfect regioselectivities. The key to the regioselectivity of this reaction was the use of 4-trifluoromethyl benzyl imines as a substrate. The products were successfully derivatised into the more functionalised molecules in good yields.

PROCESS FOR THE PREPARATION OF N-IODOAMIDES

The present invention provides new stable crystalline N-iodoamides - 1-iodo- 3,5,5-trimethylhydantoin (1-ITMH) and 3-iodo-4,4-dimethyl-2-oxazolidinone (IDMO). The present invention further provides a process for the preparation of organic iodides using N-iodoamides of this invention and recovery of the amide co-products from waste water.

Highly enantioselective copper-catalyzed alkylation of β-ketoesters and subsequent cyclization to spirolactones/bi-spirolactones

Cu-catalyzed enantioselective alkylation of β-ketoesters using alcohols for in situ preparation of alkylating reagents is reported. A number of functionalized β-ketoesters containing a quaternary carbon stereocenter are obtained with up to 99% ee. The alkylation products derived from 2-substituted allylic alcohols or their corresponding iodides can then be converted to spirolactones, bi-spirolactones, and related chiral target products.

Allyl and benzyl iodides by the anomalous action of iodotrimethylsilane

Iodotrimethylsilane (TMSI), routinely used for the dealkylation of ethers and esters, has been found to efficiently convert allyl and benzyl phosphotriesters into the corresponding iodides under mild, Bronsted-neutral conditions. In contrast, alkyl and aryl phosphotriesters were dealkylated to the corresponding phosphates under identical conditions.

New iodination reactions of saturated hydrocarbons

Unactivated C-H bonds react with iodine when exposed to trimethylsilyl azide in the presence of a hypervalent iodine reagent or, alternatively, to aqueous H2O2, acetic anhydride, and sodium azide (see scheme). (Chemical Equation Presented).

Silica chloride in the presence of NaI is a useful system for the efficient and selective conversion of TMS, TBDMS and THP ethers into their corresponding iodides

Direct and highly selective conversion of benzylic, allylic and propargylic TMS, TBDMS and THP ethers into their corresponding iodides with the SiO2-Cl/NaI system is described. Reactions were conducted in CH3CN at room temperature. Aliphatic silyl and tetrahydropyranyl ethers remained almost intact under similar reaction conditions.

A practical procedure for the synthesis of esonarimod, (R,S)-2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid, an antirheumatic agent (part 1).

An efficient and practical procedure for the synthesis of esonarimod, (R,S)-2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid (1), a new antirheumatic drug, has been developed. The intermediate, 2-methylene-4-(4-methylphenyl)-4-oxobutanoic acid (2), was prepared by Friedel-Crafts acylation of toluene with itaconic anhydride (3) in the presence of aluminum trichloride and nitrobenzene in 63% yield without silica gel column purification. Compound 1 was prepared by Michael addition of 2 with thioacetic acid (4) in 74% yield. Overall, 1 was obtained in 47% yield from 3. The structures and synthetic mechanisms of by-products (five compounds) of 2 were also clarified.