Category: 914225-70-0

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 914225-70-0, name is 1-(5-Fluoro-2-iodophenyl)ethanone, A new synthetic method of this compound is introduced below., Safety of 1-(5-Fluoro-2-iodophenyl)ethanone

Under a nitrogen atmosphere, a solution of compound 1 (2.6 g, 10 mmol) in methanol (50 mL) was cooled in an ice-water bath, into which NaBH4 (0.38 g, 10 mmol) was poured slowly, and continued to react at 0C for 5 minutes. 0.5M HCl solution was added dropwise slowly until no bubbles appeared in the reaction system. The reaction solution was adjusted to pH > 7 with saturated sodium bicarbonate solution, and extracted with ethyl acetate to obtain 2.6 g of a white solid product with a yield of 99%. LC-MS (APCI): m/z = 267 (M+1)+; 1H NMR (300 MHz, CDCl3)(delta/ppm)7.76-7.71 (m, 1H), 7.35-7.31 (m, 1H), 6.78-6.72 (m, 1H), 5.05-4.99 (m, 1H), 1.45 (d, J=6.0 Hz, 3H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Shenzhen Targetrx, Inc.; WANG, Yihan; LI, Huanyin; (30 pag.)EP3415518; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 914225-70-0, name is 1-(5-Fluoro-2-iodophenyl)ethanone, molecular formula is C8H6FIO, 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. Formula: C8H6FIO

Step 1 : A solution of (-)-DIPCI ((-)-B-chlorodiisopinocampheylborane) (57.1 g, 178 mmol) in THF (tetrahydrofuran) (100 ml) was cooled to -20 to -30 C. A solution of compound 1 (31 .3 g, 1 19 mmol) in THF (100 ml) was then added dropwise, via addition funnel (30 min addition). The reaction was left to warm up to room temperature (RT). After 2 h, the reaction was cooled to -30 C and another portion of (-)-DIPCI (38.0 g, 1 19 mmol) was added. After 30 min, the reaction was allowed to warm to RT and after 1 h, the solvents were removed in vacuo and the residue re-dissolved in MTBE (methyl tertiary-butyl ether) (200 ml). A solution of diethanolamine (31 g, 296 mmol) in ethanol/THF (15 ml/30 ml) was added via addition funnel, to the reaction mixture under an ice bath. The formation of a white precipitate was observed. The suspension was heated at reflux for 2 hours then cooled to room temperature, filtered and the mother liquids concentrated in vacuo. The residue was suspended in heptane/EtOAc (7:3, 200 ml) and again filtered. This procedure was repeated until no more solids could be observed after the liquids were concentrated. The final yellow oil was purified by column chromatography (eluent: cyclohexane/EtOAc 99:1 to 96:4). The resulting colorless oil was further purified by recrystallization from heptanes, to give alcohol compound 2 (25 g, 80% yield, 99% purity and 96% ee) as white crystals. 1H NMR (400 MHz, CDCI3) delta 7.73 (dd, 1 H), 7.32 (dd, 1 H), 6.74 (ddd, 1 H), 4.99 – 5.04 (m, 1 H), 2.01 (d, 1 H), 1 .44 (d, 3 H). LCMS-ES: No ionization, Purity 99%. Chiral GC (column CP-Chirasil-DexnCB): 96% ee; Rt (minor) 17.7 minutes and Rt (major) 19.4 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 914225-70-0, its application will become more common.

Reference:
Patent; PFIZER INC.; JENSEN, Andrew, James; LUTHRA, Suman; RICHARDSON, Paul, Francis; WO2014/207606; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

914225-70-0, A common compound: 914225-70-0, name is 1-(5-Fluoro-2-iodophenyl)ethanone, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

In a 500 mL reactor, 5-fluoro-2-iodoacetophenone (39.6 g, 150 mmol) was added.Glyoxylic acid monohydrate (13.9 g, 151 mmol), heating the reaction and distilling off water (95 , 0.1 Mpa) under reduced pressure for 3 hours.The reaction mixture was cooled to room temperature, 5% aqueous potassium carbonate solution (300 mL), and extracted twice with ethyl acetate,After 200 mL of water, the aqueous layer was acidified (10% hydrochloric acid, 300 mL), and then extracted twice with ethyl acetate.200 mL each time, the organic phase was combined, washed with brine and dried over anhydrous sodium sulfate.The solvent was removed under reduced pressure to give an orange solid.The solid was dissolved in glacial acetic acid (50 mL), concentrated hydrochloric acid (36%, 5mL).Acetic acid under reduced pressure, the residue was extracted (300 mL) with ethyl acetate, washed with brine three times,100 mL each time, the organic phase was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.To give the desired product (26.89g, 56%) as a yellow solid, M.P.146 degrees.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-(5-Fluoro-2-iodophenyl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Health Medical School; Huang Gang; Li Bin; (101 pag.)CN109705124; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

914225-70-0,Some common heterocyclic compound, 914225-70-0, name is 1-(5-Fluoro-2-iodophenyl)ethanone, molecular formula is C8H6FIO, 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.

Preparation 1051-(2-Acetyl-4-fl ro-phenyl)-pyrrolidin-2-one1 ,4-Dioxane (50 ml_) was degassed by heating briefly to reflux and bubbling nitrogen gas through the solvent for 10 minutes, whilst it cooled to room temperature. Cul (180 mg, 5 mol%), glycine (284 mg, 20 mol%), 2-pyrrolidinone (1.73ml_, 22.73 mmol), K3PO4 (10.05 g, 47.35 mmol) and 1-(5-fluoro-2-iodo-phenyl)-ethanone (5.0 g, 18.94 mmol) were added sequentially to the solvent and the reaction mixture was heated at 100C under N2 for 10 hours. The reaction mixture was filtered through a celite plug, eluting with EtOAc and the filtrate was concentrated. The crude product was purified by flash chromatography (5% MeOH in DCM) to give the title compound (2.02 g, 48% yield) as a yellow oil1H NMR (400 MHz, CDCI3): delta ppm 2.20 (2H, pentet), 2.47 (2H, t), 2.54 (3H, s), 3.83 (2H, t), 7.17-7.21 (2H ,m), 7.28-7.32 (1 H, m). MS:: m/z 222 [MH]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(5-Fluoro-2-iodophenyl)ethanone, its application will become more common.

Reference:
Patent; PFIZER INC.; BUNNAGE, Mark, Edward; COOK, Andrew, Simon; CUI, Jingrong, Jean; DACK, Kevin, Neil; DEAL, Judith, Gail; GU, Danlin; HE, Mingying; JOHNSON, Patrick, Stephen; JOHNSON, Ted, William; LE, Phuong, Thi, Quy; PALMER, Cynthia, Louise; SHEN, Hong; WO2011/138751; (2011); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 914225-70-0, name is 1-(5-Fluoro-2-iodophenyl)ethanone, 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 914225-70-0, 914225-70-0

Step 1 : A solution of (-)-DIPCI (57.1 g, 178 mmol) in THF (100 ml) was cooled to -20 to -30 C. A solution of compound 1 (31 .3 g, 1 19 mmol) in THF (100 ml) was then added dropwise, via addition funnel (30 min addition). The reaction was left to warm up to RT. After 2 h, the reaction was cooled to -30 C and another portion of (-)-DIPCI (38.0 g, 1 19 mmol) was added. After 30 min, the reaction was allowed to warm to RT and after 1 h, the solvents were removed in vacuo and the residue re-dissolved in MTBE (200 ml). A solution of diethanolamine (31 g, 296 mmol) in ethanol/THF (15 ml/30 ml) was added via addition funnel, to the reaction mixture under an ice bath. The formation of a white precipitate was observed. The suspension was heated at reflux for 2 hours then cooled to room temperature, filtered and the mother liquids concentrated in vacuo. The residue was suspended in heptane/EtOAc (7:3, 200 ml) and again filtered. This procedure was repeated until no more solids could be observed after the liquids were concentrated. The final yellow oil was purified by column chromatography (eluent: cyclohexane/EtOAc- 99:1 to 96:4). The resulting colorless oil was further purified by recrystallisation from heptanes, to give alcohol compound 2 (25 g, 80% yield, 99% purity and 96% ee) as white crystals. 1H NMR (400 MHz, CDCI3) delta 7.73 (dd, 1 H), 7.32 (dd, 1 H), 6.74 (ddd, 1 H), 4.99 – 5.04 (m, 1 H), 2.01 (d, 1 H), 1.44 (d, 3 H). LCMS-ES: No ionization, Purity 99%. Chiral GC (column CP-Chirasil-DexnCB): 96% ee; Rt (minor) 17.7 minutes and Rt (major) 19.4 minutes.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-(5-Fluoro-2-iodophenyl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William; WO2013/132376; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com