Category: 869365-97-9

Electric Literature of 869365-97-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 869365-97-9, name is (5-Chloro-2-iodophenyl)(2,6-difluorophenyl)methanone belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

{3-[4-Chloro-2-(2,6-difluoro-benzoyl)-phenyl]-prop-2-ynyl}-carbamic acid tert-butyl ester (3aa) (5-Chloro-2-iodo-phenyl)-(2,6-difluoro-phenyl)-methanone (2aa) (5.5 g, 14.5 mmol), prop-2-ynyl-carbamic acid tert-butyl ester (2.5 g, 16 mmol), PdCl2(PPh3)2 (0.6 g, 0.9 mmol) and Cu(I)I (0.2 g, 0.9 mmol) were suspended in anhydrous CH2Cl2 (50 mL) and the mixture was sparged with nitrogen for 30 min. Diethylamine (8 mL) was added and the solution was stirred at room temperature for 16 h. The solution was concentrated in vacuo and the resulting residue purified by column chromatography (silica gel, 0 to 15% EtOAc/hexanes) to afford 3aa (3.6 g, 61%) as a white solid, MS m/z=406 (M+H).

The synthetic route of (5-Chloro-2-iodophenyl)(2,6-difluorophenyl)methanone has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2005/256102; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 869365-97-9, These common heterocyclic compound, 869365-97-9, name is (5-Chloro-2-iodophenyl)(2,6-difluorophenyl)methanone, 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.

(5-chloro-2-iodophenyl)(2-fluoro-6-methoxyphenyl)methanone (3)[0148] Into a reactor at room temperature was added 2 (67.6kg, 179mol) and MTBE (344L). The mixture was warmed to 40 C and stirred for 30rnin until solids fully dissolved. The mixture was then cooled to 25 to 30 C. Sodium methoxide as a 25% w/w solution in methanol (45.2kg, 209mol) was added over a minimum of 90min at 25 to 30 C. The reaction mixture was stirred for at least 2h until >99.0% conversion was obtained by HPLC analysis. Water (483L) was added slowly over 30min while maintaining the temperature between 20 and 25 C. The layers were separated and the aqueous phase was extracted with MTBE (77L). The combined organic extracts were washed with a dilute brine solution (38kg NaCl in 342L water). The organic layer was filtered, washed with water (242L) and the organic phase was filtered. The resulting organic phase was concentrated until 360L of solvent were removed while maintaining the internal temperature below 70 C. Isobutanol (302L) was added and the mixture was concentrated while maintaining the internal temperature below 70 C until 307L of solvent were removed. A second portion of isobutanol (330L) was added and the mixture was concentrated while maintaining the internal temperature below 70 C until 210L of solvent were removed. The mixture was heated to 60 to 85 C until a clear solution was obtained and cooled to 50 C. A slurry of seed crystals (50g in 150mL isobutanol) was added and the mixture was cooled to 40 C. A second slurry of seed crystals (30g in 60mL isobutanol) was added and the mixture was cooled to 20 to 25 C over a minimum of 3h. The resulting mixture was stirred an additional 2h. The mixture was filtered and washed with isobutanol (2 x 65L). The resulting wet cake was dried at 20 to 35 C under vacuum to provide 50.9kg of crude 3. Into a separate reactor was charged crude 3 and isobutanol (69L). The mixture was heated to 75 to 80 C until a clear solution was obtained. The reaction mixture was cooled to 55 C and a slurry of seed crystals (50g in 500mL isobutanol) was added. The mixture was stirred for 30rnin at 55 C, cooled to 20 to 25 C over a minimum of 3h and stirred an additional 2h. The mixture was filtered and washed with isobutanol (2 x 31L). The wet cake was dried under vacuum at 40 C to provide 46.0kg (66% yield) of purified 3. ? NMR (300 MHz, CDCL) delta 7.88 (d, J=8.2 Hz, 1H), 7.42 (m, 2H), 7.13 (dd, J=2.3, 8.2 Hz), 6.76 (m, 2H), 3.73 (s, 3H); MS (ESI) m/z 391.2 (M + H+, 30%).

Statistics shows that (5-Chloro-2-iodophenyl)(2,6-difluorophenyl)methanone is playing an increasingly important role. we look forward to future research findings about 869365-97-9.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; ARMITAGE, Ian; COOPER, Martin, I.; EDDLESTON, Mark, D.; FAIBER, Neil, C.; MCCUBBIN, Quentin, J.; WATT, Stephen, W.; WO2011/103089; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com