Category: 3032-81-3

3032-81-3, These common heterocyclic compound, 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: 2-Phenylimidazo[1,2-a]pyrazine 2 (1.0 mmol) was introducedinto a 10 mL vial with (hetero)arylhalide (2.0 mmol), palladiumacetate (0.04 mmol), tricyclohexylphosphine tetrafluoroborate(0.08 mmol), pivalic acid (0.6 mmol) and potassium carbonate(3.0 mmol) in N,N-dimethylacetamide (4 mL). The vial was purgedwith argon for 10 min and then sealed. The mixture was heated at100 C for 18e40 h and then it was cooled to room temperature.Water was added and the aqueous layer was extracted with ethylacetate (2 x 10 mL). The combined organic extracts were washedwith brine and water, dried over sodium sulfate, filtered, concentratedin vacuo and purified by silica gel column chromatography.Trituration with diisopropylic ether afforded the compounds 4aeg.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3032-81-3.

Reference:
Article; Marchand, Pascal; Bazin, Marc-Antoine; Pagniez, Fabrice; Riviere, Guillaume; Bodero, Lizeth; Marhadour, Sophie; Nourrisson, Marie-Renee; Picot, Carine; Ruchaud, Sandrine; Bach, Stephane; Baratte, Blandine; Sauvain, Michel; Pareja, Denis Castillo; Vaisberg, Abraham J.; Le Pape, Patrice; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 381 – 395;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., 3032-81-3

To an oven dried 8 mL vial with teflon cap purged with N2 was added Zinc dust (298 mg, 4.56 mmol), DMF(1.5 mL), and iodine (57.8 mg, 0.228 mmol). To this mixture was added (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate (500 mg, 1.519 mmol), immediately followed by iodine (57.8 mg, 0.228 mmol).Pd2(dba)3 (69.6 mg, 0.076 mmol), 2-DICYCLOHEXYLPHOSPHINO-2?,6?-DIMETHOXYBIPHENYL(62.4 mg, 0.152 mmol), 1,3-dichloro-5-iodobenzene (622 mg, 2.279 mmol) and the reaction mixture wasallowed to stir at rt for 16 h. The crude mixture was diluted in EtOAc (30 mL) and DMF was removed withfour aqueous washes. The organic phase was dried over anhydrous sodium sulfate. The solution was filteredand concentrated, and the crude was purified by silica gel chromatography using 100percent hexanes to 30percentEtOAc/Hexanes. The desired product was obtained as a pale yellow oil, (S)-methyl 2-((tertbutoxycarbonyl)amino)-3-(3,5-dichlorophenyl)propanoate, 0.160 g yield in 77percent purity by LCMS analysis.Analysis LCMS condition F: Retention time=2.84 min; ESI-MS(+) m/z 348.1 (M+H).

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Reference:
Patent; Bristol-Myers Squibb Company; Miller, Michael Matthew; Mapelli, Claudio; Allen, Martin Patrick; Bowsher, Michael S.; Boy, Kenneth M.; Gillis, Eric P.; Langley, David R.; Mull, Eric; Poirier, Maude A.; Sanghvi, Nishith; Sun, Li-Qiang; Tenney, Daniel J.; Yeung, Kap-Sun; Zhu, Juliang; Reid, Patrick C.; Scola, Paul Michael; (892 pag.)US9308236; (2016); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

3032-81-3, Adding a certain compound to certain chemical reactions, such as: 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 3032-81-3.

To a solution of 3,5-dichloro iodobenzene (1.8 g, 6.6 mmol) in diethyl ether (20 ml) cooled to -78¡ã C. is added n-BuLi (2.8 ml of a 2.5 M solution in hexane, 6.8 mmol). The reaction mixture is stirred at -78¡ã C. for 10 min, allowed to warm to 25¡ã C. and added in three portions to a solution of N-t-butoxycarbonyl-3-ketopiperidine (598 mg, 3.01 mmol) in diethyl ether (10 ml) cooled to 0¡ã C. The reaction mixture is stirred at 25¡ã C. for 30 min. The reaction mixture is diluted with ethyl acetate, washed with 1 N KHSO4, water and brine, dried over sodium sulfate and concentrated in vacuo. The crude product is purified by flash chromatography (silica gel, 30percent to 50percent ethyl acetate in hexane) to give N-t-butoxycarbonyl-3-(3,4-dichlorophenyl)-3-hydroxy piperidine (150 mg).

According to the analysis of related databases, 3032-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nantermet, Philippe G.; Barrow, James C.; Selnick, Harold G.; US2001/44454; (2001); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com