- PROCESS FOR SYNTHESIS OF PICOLINAMIDES
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The present technology relates to processes, mixtures and intermediates useful for making picolinamide fungicides. The picolinamide compounds are prepared by processes that include coupling together a 4-methoxy-3-acyloxypicolinic acid with key 2-amino-L-alaninate esters derived from substituted 2-phenylethanols.
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Paragraph 0208-0213
(2021/04/23)
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- Regioselective 1,4-conjugate addition of grignard reagents to nitrodienes in the presence of catalytic amounts of Zn(II) salts
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Grignard reagents undergo facile regioselective 1,4-conjugate addition to nitrodienes in the presence of catalytic amounts of Zn(II) salts with excellent yields. A wide range of ligands such as alkyl, aryl, heteroaryl, allyl, vinyl, 1-alkynyl, and alkoxy ligands were transferred, while a thiolate ligand afforded 1,6-regioselectivity. The reactions were successfully carried out on δ-alkyl- or aryl-substituted α,β,γ,δ-diunsaturated nitrodiene substrates. Regioselectivity is minimally influenced by temperature or choice of solvent.
- Dhakal, Ramesh C.,Dieter, R. Karl
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supporting information
p. 1362 - 1365
(2014/04/03)
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- METHOD FOR PRODUCING BIPHENYL DERIVATIVE
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Provided is a method for producing a biphenyl derivative, with an industrially high yield and excellent productivity, by use of a raw material which is low in cost and toxicity. More specifically, the method for producing the biphenyl derivative represented by general formula (1) is characterized in that a chlorine atom in a benzene derivative represented by general formula (2) reacts with magnesium metal to convert the benzene derivative into a Grignard reagent, and then the Grignard reagent is subjected to a coupling reaction in the presence of a catalyst and a dichloropropane: and (wherein A represents at least one selected from alkyl groups, alkoxy groups, alkoxymethyl groups, a vinyl group, phenyl groups and chlorine, and n represents an integer of 1 to 4).
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Page/Page column 6-7
(2009/08/13)
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- Process safety evaluation of a magnesium-iodine exchange reaction
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An unexpected highly exothermic decomposition was observed during routine safety analysis of the magnesium-iodine exchange reaction of 2-iodo-4-fluorotoluene (3) with commercially available i-PrMgCl (2.0 M solution in THF). When the reaction mixture was scanned in an adiabatic calorimeter with the use of a 2 °C/min temperature ramp, a rapid exothermic decomposition with an onset temperature of approximately 80 °C was observed. The system temperature rapidly rose to 210 °C at a peak rate of 200 °C/min. Subsequent testing of three simplified substrates showed the same type of exothermic decomposition for all cases. Control experiments indicated that the decomposition requires both aryl iodide and i-PrMgCl (or arylMgCl and i-PrI). While the onset temperatures for all cases studied were generally well above the typical operating temperature for these reactions (0-10 °C), it is nonetheless important to cautiously evaluate these types of processes and install proper engineering controls for analogous decomposition events.
- Reeves, Jonathan T.,Sarvestani, Max,Song, Jinhua J.,Tan, Zhulin,Nummy, Laurence J.,Lee, Heewon,Yee, Nathan K.,Senanayake, Chris H.
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p. 1258 - 1262
(2012/12/23)
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- Process for preparing 4'-trifluoromethyl-2-methylbiphenyl and 4'-trifluoromethyl-biphenyl-2-carboxylic acid from o-tolylmetallates
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The invention relates to a process for preparing a compound of the formula (I) in which R is methyl or carboxyl, which comprises coupling an ortho-tolylmetallate of the formula (II) with a compound of the formula (III) in which M is —MgF, —MgCl, —MgBr, —Mgl, —Li, —ZnF, —ZnCl, —ZnBr or —Znl and X is F, Cl, Br, I, N2+, straight-chain or branched (C1-C20)-alkoxy, arylsulfonate or alkylsulfonate in the presence of an Ni, Pd or platinum metal catalyst to give a compound of the formula (I) where R is CH3 and, if appropriate, oxidizing the compound of the formula (I) where R is CH3 to give the compound of the formula (I) where R is carboxyl.
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- Production methods of alpha, alpha, alpha-trifluoromethylphenyl-substituted benzoic acid and intermediate therefor
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The present invention relates to a production method of compound [V] useful as an intermediate for medicaments and agrochemicals. The method includes reacting compound [III] with hexamethylenetetramine under heating to give compound [IV], and oxidizing the obtained compound [IV] with a halous acid salt or a ruthenium compound. According to the present invention, moreover, an organometallic compound having a tolyl group and compound [I] are cross-coupled in the presence of a catalyst to give compound [II] useful as an intermediate for medicaments and agrochemicals. The compound [II] is halogenated to give compound [III]. wherein X is halogen atom.
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