Category: 320407-92-9

Danner, Paulami; Bauer, Matthias; Phukan, Prodeep; Maier, Martin E. published the artcile< Total synthesis of cryptophycin 3>, COA of Formula: C8H8BrClO, the main research area is cyclodepsipeptide peptidomimetic cryptophycin analog total synthesis; glycine derivative stereoselective alkylation phenylalanine subunit preparation; oxidation Witting reaction hydroxy ester preparation seco acid esterification; peptide coupling Fmoc protection macrolactamization.

The depsipeptide cryptophycin 3 and the cryptophycin analog [I (R1 = Cl, R2 = OMe; R1 = R2 = H)] were prepared from the corresponding four subunits using Fmoc (Fmoc = 9-fluorenylmethyloxycarbonyl) protecting group for the amino functions. The phenylalanine derivative for cryptophycin 3 [subunit B (II)] was prepared by stereoselective alkylation of glycine derivative The tripeptide analogs, which contains fragments D and C was acquired from the starting amino ester III. After extension at the carboxyl function by esterification with the hydroxy ester III, the seco compounds IV (R1 = Cl, R2 = OMe; R1 = R2 = H) were deprotected and submitted to ring closure by macrolactamization in the presence of TBTU as condensing agent.

European Journal of Organic Chemistry published new progress about (Fluorenylmethoxy)carbonyl group. 320407-92-9 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H8BrClO, COA of Formula: C8H8BrClO.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Naik, R. G.; Wheeler, T. S. published the artcile< Reactivity of the ω-halogen atom in p-alkoxybenzyl halides: preparation of phenylacetic acids>, Formula: C8H8BrClO, the main research area is .

6-Chloropiperonal (I) and PhNH2 at 100° give 6-chloropiperonylideneaniline, m. 112°; 6-Br analog, m. 131-2°; 3-chloro-4-methoxybenzylideneaniline, m. 85°; 3-Br analog, m. 96-7°. I (25 g.), treated with 100 g. 50% NaOH and 5 cc.EtOH and kept overnight, gives 10 g. of 6-chloro-3,4-methylenedioxybenzyl alc. (II), m. 73-4°; 6-Br analog (III), m. 90°; 3-chloro-4-methoxybenzyl alc. (IV), b10 178-80°; 3-Br analog (V), m. 63-4°. Evaporation of 15 g.II in 75 cc. C6H6 saturated with HCl (at 0°) gives 14 g. of 6-chloro-3,4-methylenedioxybenzyl chloride (VI), m. 65°; shaking 10 g.II with 50 g.HBr (d. 1.69) gives 10 g. of the bromide, m. 75-6°. Similarly III gives a chloride, m. 64-5°, and a bromide, m. 94°; the chloride from IV b6 145-7° and the bromide, m. 52-3°. V yields a chloride, m. 51-2°, and a bromide, m. 61-2°. Refluxing 2 g. of VI with KI in Me2CO-H2O for 1.5 hrs. gives 1.6 g. of the iodide of II, yellow, m. 95-6°; iodide of III, m. 90-1°; of IV, m. 61-2°; of V, m. 64-5°. VI (16 g.), KCN and EtOH, shaken 24 hrs., give 9.5 g. of 6-chloropiperonylacetonitrile (VII), b15 190°, m. 70-1°; 6-Br analog, m. 71-2°; 3-chloro-p-anisylacetonitrile, m. 54-5°; 3-Br analog, m. 56-7°. Refluxing 7 g. of VII with NaOH in diluteEtOH for 8 hrs. gives 6 g. of 6-chloropiperonylicacetic acid, m. 174-5°; Me ester, m. 69-70°; Et ester, m. 60-1°; 6-Br analog, m. 190°; Et ester, m. 69-70°. 3-Chloro-p-anisylacetic acid, m. 95-6°; 3-Br analog, m. 114-15°. 3,4-Cl(MeO)C6H3CH2Cl (2.5 g.) and MeOH, refluxed 2 hrs., give 1.8 g. of 3-chloro-4-methoxybenzyl Me ether, b5 135-40°; Et ether, b10 150-5°; 3-bromo-4-methoxybenzyl Et ether, b10 155-60°; the ethers regenerate the halides on treatment with HCl-C6H6 or concentratedHBr. Heating 3,4-CH2O2C6H3CH2Br (VIII) with MeOH or EtOH for 6 hrs. gives 2,3,6,7-bismethylenedioxy-9,10-dihydroanthracene (Ewins, C. A. 4, 195); its formation is apparently catalyzed by acids, for refluxing VIII with MeOH and a little Na2CO3 gives 3,4-methylenedioxybenzyl Me ether, b10 120. The 6-halogen derivatives of VIII react with alcs. without formation of dihydroanthracenes but the oils obtained always contain more halogen than the expected ethers; the 6-NO2 derivative of VIII did not react with alcs. VI (6 g.) and 12 g.PCl5, heated 4 hrs. at 120°, give 5 g. of 6-chloro-3,4-dichloromethylenedioxybenzyl chloride (IX), b10 150-4°; addition of cold H2O after 5 min. to its solution in HCO2H gives 6-chloro-3,4-carbonyldioxybenzyl chloride (X), m. 64°. 6-Br analog of IX, b10 155-7°; of X, m. 80-1°.

Journal of the Chemical Society published new progress about Halogens. 320407-92-9 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H8BrClO, Formula: C8H8BrClO.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Naik, R. G.; Wheeler, T. S. published the artcile< Reactivity of the ω-halogen atom in p-alkoxybenzyl halides: preparation of phenylacetic acids>, Formula: C8H8BrClO, the main research area is .

6-Chloropiperonal (I) and PhNH2 at 100° give 6-chloropiperonylideneaniline, m. 112°; 6-Br analog, m. 131-2°; 3-chloro-4-methoxybenzylideneaniline, m. 85°; 3-Br analog, m. 96-7°. I (25 g.), treated with 100 g. 50% NaOH and 5 cc.EtOH and kept overnight, gives 10 g. of 6-chloro-3,4-methylenedioxybenzyl alc. (II), m. 73-4°; 6-Br analog (III), m. 90°; 3-chloro-4-methoxybenzyl alc. (IV), b10 178-80°; 3-Br analog (V), m. 63-4°. Evaporation of 15 g.II in 75 cc. C6H6 saturated with HCl (at 0°) gives 14 g. of 6-chloro-3,4-methylenedioxybenzyl chloride (VI), m. 65°; shaking 10 g.II with 50 g.HBr (d. 1.69) gives 10 g. of the bromide, m. 75-6°. Similarly III gives a chloride, m. 64-5°, and a bromide, m. 94°; the chloride from IV b6 145-7° and the bromide, m. 52-3°. V yields a chloride, m. 51-2°, and a bromide, m. 61-2°. Refluxing 2 g. of VI with KI in Me2CO-H2O for 1.5 hrs. gives 1.6 g. of the iodide of II, yellow, m. 95-6°; iodide of III, m. 90-1°; of IV, m. 61-2°; of V, m. 64-5°. VI (16 g.), KCN and EtOH, shaken 24 hrs., give 9.5 g. of 6-chloropiperonylacetonitrile (VII), b15 190°, m. 70-1°; 6-Br analog, m. 71-2°; 3-chloro-p-anisylacetonitrile, m. 54-5°; 3-Br analog, m. 56-7°. Refluxing 7 g. of VII with NaOH in diluteEtOH for 8 hrs. gives 6 g. of 6-chloropiperonylicacetic acid, m. 174-5°; Me ester, m. 69-70°; Et ester, m. 60-1°; 6-Br analog, m. 190°; Et ester, m. 69-70°. 3-Chloro-p-anisylacetic acid, m. 95-6°; 3-Br analog, m. 114-15°. 3,4-Cl(MeO)C6H3CH2Cl (2.5 g.) and MeOH, refluxed 2 hrs., give 1.8 g. of 3-chloro-4-methoxybenzyl Me ether, b5 135-40°; Et ether, b10 150-5°; 3-bromo-4-methoxybenzyl Et ether, b10 155-60°; the ethers regenerate the halides on treatment with HCl-C6H6 or concentratedHBr. Heating 3,4-CH2O2C6H3CH2Br (VIII) with MeOH or EtOH for 6 hrs. gives 2,3,6,7-bismethylenedioxy-9,10-dihydroanthracene (Ewins, C. A. 4, 195); its formation is apparently catalyzed by acids, for refluxing VIII with MeOH and a little Na2CO3 gives 3,4-methylenedioxybenzyl Me ether, b10 120. The 6-halogen derivatives of VIII react with alcs. without formation of dihydroanthracenes but the oils obtained always contain more halogen than the expected ethers; the 6-NO2 derivative of VIII did not react with alcs. VI (6 g.) and 12 g.PCl5, heated 4 hrs. at 120°, give 5 g. of 6-chloro-3,4-dichloromethylenedioxybenzyl chloride (IX), b10 150-4°; addition of cold H2O after 5 min. to its solution in HCO2H gives 6-chloro-3,4-carbonyldioxybenzyl chloride (X), m. 64°. 6-Br analog of IX, b10 155-7°; of X, m. 80-1°.

Journal of the Chemical Society published new progress about Halogens. 320407-92-9 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H8BrClO, Formula: C8H8BrClO.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Tan, Zhenda; Xiong, Biao; Yang, Jian; Ci, Chenggang; Jiang, Huanfeng; Zhang, Min published the artcile< Selective reductive cross-coupling of N-heteroarenes by an unsymmetrical PNP-ligated manganese catalyst>, HPLC of Formula: 320407-92-9, the main research area is tetrahydronaphthyridine preparation regioselective chemoselective; indole naphthyridine reductive cross coupling manganese catalyst; pyrrole naphthyridine reductive cross coupling manganese catalyst; heteroarene naphthyridine reductive cross coupling manganese catalyst.

Herein, by developing an unprecedented manganese catalyst ligating with an unsym. 2-aminotetrahydronaphthyridyl PNP-ligands e.g., I, a new reductive cross-coupling of indoles II (R = H, 5-MeO, 7-Me, 2,5-di-Me, etc.)/1H-pyrrole, 2,5-dimethyl-1H-pyrrole and N-heteroarenes III (R1 = H, 2,3-di-Me, 4-chlorophenyl, thiophen-2-yl, etc.; X = CH, N) was achieved. Mechanistic investigations show that the catalyst-enabled in situ capture of the partially reduced intermediates by interruption of the second transfer hydrogenation of N-heteroarenes constitutes the key to success for the present reaction. The developed chem. proceeds with good substrate and functional group compatibility, high step and atom efficiency, and excellent chemo and regioselectivity, and is applicable for late-stage modification of pyridine-containing biomedical mols., which has established a new platform allowing the linkage of aromatic systems into functional frameworks, and further development of unsym. PNP organometallic complexes and related catalytic transformations.

Journal of Catalysis published new progress about Aromatic nitrogen heterocycles Role: SPN (Synthetic Preparation), PREP (Preparation). 320407-92-9 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H8BrClO, HPLC of Formula: 320407-92-9.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Wang, Qian; Tao, Quan; Dong, Hui; Ni, Chuanfa; Xie, Xiaoming; Hu, Jinbo published the artcile< Fluorination Triggers Fluoroalkylation: Nucleophilic Perfluoro-tert-butylation with 1,1-Dibromo-2,2-bis(trifluoromethyl)ethylene (DBBF) and CsF>, Recommanded Product: 4-(Bromomethyl)-2-chloro-1-methoxybenzene, the main research area is electrophile fluorination fluoroalkylation dibromo bistrifluoromethylethylene magnetic resonance imaging safety; perfluoro tert butylated compound preparation; fluorination; fluoroalkylation; imaging probes; magnetic resonance imaging; perfluoro-tert-butylation.

Perfluoro-tert-butylation reaction has long remained a challenging task. We now report the use of 1,1-dibromo-2,2-bis(trifluoromethyl)ethylene (DBBF, I) as a practical reagent for perfluoro-tert-butylation reactions for the first time. Through a consecutive triple-fluorination process with DBBF and CsF, the (CF3)3C- species can be liberated and observed, which is able to serve as a robust nucleophilic perfluoro-tert-butylating agent for various electrophiles. The power of this synthetic protocol is evidenced by the efficient synthesis of structurally diverse perfluoro-tert-butylated mols. Multiple applications demonstrate the practicability of this method, as well as the superiority of perfluoro-tert-butylated compounds as sensitive probes. The perfluoro-tert-butylated product was successfully applied in 1H- and 19F-magnetic resonance imaging (MRI) experiment with an ultra-low field (ULF) MRI system.

Angewandte Chemie, International Edition published new progress about Electrophiles. 320407-92-9 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H8BrClO, Recommanded Product: 4-(Bromomethyl)-2-chloro-1-methoxybenzene.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Tan, Zhenda; Ci, Chenggang; Yang, Jian; Wu, Yang; Cao, Liang; Jiang, Huanfeng; Zhang, Min published the artcile< Catalytic Conversion of N-Heteroaromatics to Functionalized Arylamines by Merging Hydrogen Transfer and Selective Coupling>, Reference of 320407-92-9, the main research area is azaarene alkyl bromide amino arylmethanol ruthenium hydrogen transfer coupling; alkylaminoaryl methylazaarene preparation chemoselective.

A ruthenium-catalyzed deconstruction of N-heteroaromatics to functionalized arylamines with 2-aminoaryl methanols via hydrogen transfer and selective coupling was reported. The reaction was achieved via sequential functionalization of the β and α-sites of the initially formed N-heteroarenium salts followed by a C-N cleavage, proceeding with the striking features of broad substrate scope, excellent functional groups tolerance, high chemoselectivity and atom-efficiency, and applicable for streamline synthesis of some biomedical mols. The strategy utilized will pave the avenues for further development of catalytic transformations of inert organo-systems to functional frameworks.

ACS Catalysis published new progress about Amino alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 320407-92-9 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H8BrClO, Reference of 320407-92-9.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics