Month: July 2021

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. 5460-32-2, name is 4-Iodo-1,2-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H9IO2

3-[4-(3,4-Dimethoxyphenyl)-but-3-ynyl]-1,3-oxazolidin-2-one (34). Triethylamine (0.08 mL, 0.574 mmol) and Pd(PPh3)Cl2 (8.0 mg, 0.011 mmol) were added to a mixture of 3,4-dimethoxyphenyl iodide (33) (64 mg, 0.242 mmol) and alkyne 25 (34 mg, 0.245 mmol) in THF (3 mL) at room temperature. Then Cu(I)I (5 mg, 0.026 mmol) was added. The resulting mixture was stirred at room temperature for 4 h. The reaction was quenched with water (10 mL) and concentrated to remove the organic solvents. The residue was diluted with ethyl acetate (15 mL). The organic layer was separated and washed with brine (2.x.10 mL), dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (25 g), eluting with EtOAc-hexanes (10-50percent) to afford the product 34 (54 mg) as solid in 80percent yield: mp 78-79° C. 1H NMR (300 MHz, CDCl3) delta 6.95 (dd, J=2.1 Hz, J=8.4 Hz, 1H), 6.88 (d, J=1.8 Hz, 1H), 6.76 (d, J=8.4 Hz, 1H), 4.32 (t, J=7.8 Hz, 2H), 3.86 (s, 3H), 3.85 (s, 3H), 3.73 (t, J=7.8 Hz, 2H), 3.51 (t, J=6.6 Hz, 2H), 2.67 (t, J=6.6 Hz, 2H); ESIMS m/z (rel intensity) 276.05 (MH+, 94), 298.05 (MNa+, 98). Anal. (C15H17NO4) C, H, N.

According to the analysis of related databases, 5460-32-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PURDUE RESEARCH FOUNDATION; US2008/300288; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 5458-84-4, 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. 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Cooled 140 mL pyridine in a large sealable vessel to -40 2C.Bubbled in trifluoromethyl iodide from a gas cylinder, whichhad been kept in freezer overnight. After adding ICF3 for20 min, added 2-iodo-5-nitroanisole (24.63 g) and copperpowder (67.25 g). Sealed vessel and stirred vigorously for22 h at 140 2C After cooling to -50 aC, carefully unsealedreaction vessel and poured onto ice and Et20. Repeatedlywashed with Et20 and H20. Allowed the ice – Et20 mixture towarm to RT. Separated layers, washed organic layer with INHC1 (3x) , then brine, dried over Na2S04, filtered andconcentrated in vacuo. Eluted material through silica gelplug (4.5:1 Hex:CH2Cl2) to provide 5-nitro-2-trifluoromethylanisole.

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-Iodo-2-methoxy-4-nitrobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; WO2006/12374; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 31599-60-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 31599-60-7 name is 1-Iodo-2,3-dimethylbenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a 25mL of oven-dried Schlenk tube equipped with a magnetic stir bar was charged with [Pd(C3H5)Cl]2 (3.7mg 0.01mmol, 0.05 equiv), XPhos (10.5mg, 0.022mmol, 0.11 equiv), K2CO3 (69.1mg, 0.5mmol, 2.5 equiv), and dry CH3CN (1mL). After stirring for about 15minat r.t. under argon, a solution of aryl iodide 1 (0.24mmol, 1.2 equiv), alkylating reagent 2 (0.2mmol, 1.0 equiv), 5-Norbornene-2-carboxylic acid N4 (5.5mg, 0.04mmol, 0.2 equiv) in dry MeCN (1mL) was added, then heated to 70C and stirred for 5-24h. The reaction was monitored by TLC, after completion of the reaction, the mixture was cooled to r.t., filtered through a thin pad of celite eluting with ethyl acetate (10mL), and the combined filtrate was concentrated in vacuo. The residue was directly purified by column chromatography on silica gel or purified by PTLC to give the desired product 3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Iodo-2,3-dimethylbenzene, and friends who are interested can also refer to it.

Reference:
Article; Liu, Ze-Shui; Qian, Guangyin; Gao, Qianwen; Wang, Peng; Cheng, Hong-Gang; Hua, Yu; Zhou, Qianghui; Tetrahedron; vol. 75; 12; (2019); p. 1774 – 1780;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 627-31-6, 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. 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), This compound has unique chemical properties. The synthetic route is as follows.

To a solution of ethyl 2-(6-nitropyridin-3-yl)acetate (33 g, 160 mmol) in DMF (150 mL) was added NaH (13 g, 330 mmol) (60 % in oil) at 0 C. The reaction mixture was stirred for 15 min while warming to RT. After 15 min the reaction mixture was cooled to 0 C and 1,3-diiodopropane (37 mL, 330 mmol) was added. After stirring at 0 C for 30 min, the reaction mixture was warmed to RT and was stirred for 1 h. After 1 h, saturated NH4C1 (500 mL) was added, followed by the addition of water (500 mL). The reaction mixture was washed with EtOAc (500 mLx3). The combined organics were washed with brine (200 mL), dried over anhydrous Na2SC>4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Petroleum ether/EtOAc =30/1 to 20/1) to afford ethyl l-(6- nitropyridin-3-yl)cyclobutanecarboxylate. MS (ESI) calc’d [M+H]+, 251; found, 251.

The chemical industry reduces the impact on the environment during synthesis 1,3-Diiodopropane(stabilized with Copper chip). I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WHITE, Catherine M.; ACHAB, Abdelghani; BHARATHAN, Indu T.; FRADERA, Xavier; HAN, Yongxin; LI, Derun; LIM, Jongwon; LIU, Kun; MCGOWAN, Meredeth Ann; SCIAMMETTA, Nunzio; YU, Wensheng; ZHANG, Hongjun; ZHOU, Hua; (107 pag.)WO2019/74749; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 2142-70-3, name is 1-(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 2142-70-3, Computed Properties of C8H7IO

General procedure: Iodobenzene (0.50mmol), phenylacetylene (0.55mmol), NaOAc (1mmol), and dimethyl sulfoxide (DMSO, 8mL) were mixed. Well-dispersed Pd/Fe3O4GO (0.4mol%) in DMSO (2mL) was added to the mixture with vigorous stirring. After the reaction, the catalyst was separated from the solution by centrifugation. The product was extracted three times with dichloromethane (20mL) and dried using MgSO4.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Kim, Miran; Kang, Hyuntae; Park, Kang Hyun; Catalysis Communications; vol. 72; (2015); p. 150 – 155;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 375-80-4, 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. 375-80-4, name is 1,6-Diiodoperfluorohexane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

55.4 g (0.10 mol) of IC 6 F 12 I obtained in Reference Example 1 and 0.58 g (0.004 mol) of tert-butyl peroxide were added to a reactor having a capacity of 150 ml equipped with a stirrer and a thermometer. Next, VDF was added under reduced pressure until reaching 0.5 MPa, and then heating was carried out at 125 C. for 3 hours. Further, after cooling the reaction solution to 70 C., VDF was added to 0.5 MPa and heated at 125 C. for 3 hours. Further, after cooling the reaction solution to 70 C., VDF was added until it reached 0.5 MPa and heated at 125 C. for 5 hours. A total amount of 12.2 g (0.19 mol) of VDF was fed to the reactor.After cooling and discharge of the residual gas, 300 g of chloroform and 20.2 g (0.20 mol) of triethylamine were added to this product, and the reaction was carried out at 35 C. for 3 hours. 150 g of water and 25 g of a 10% hydrochloric acid aqueous solution were added to the obtained reaction solution, and the liquid separation operation was carried out to obtain an organic layer.Chloroform was distilled off from the organic layer, then distilled,17.8 g (yield 42%) of a 6E-T 2 T fraction (purity 99%) having a boiling point of 76 C. (13.33 kPa) of the following formula (12)3.6 g (yield 7%) of a 6E-1 T fraction (purity 97%) having a boiling point of 63 C. (4.00 kPa) of the following formula (13)9.8 g (yield 20%) of a 6E-T 3 TT fraction (purity 97%) having a boiling point of 74 C. (4.00 kPa) of the following formula (14) and 6 E- 0.8 g (yield 1%) of 2TT fraction (purity 98%) was obtained.The structure of the obtained fraction was confirmed by 1 H-NMR and 19 F-NMR.

The synthetic route of 1,6-Diiodoperfluorohexane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tosoh F-Tech Co., Ltd.; Kondo, Norihisa; Kono, Masahiro; (14 pag.)JP2015/81232; (2015); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 59528-27-7,Some common heterocyclic compound, 59528-27-7, name is (4-Iodophenyl)methanamine hydrochloride, molecular formula is C7H9ClIN, 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.

A mixture of (4-iodophenyl)methanamine hydrochloride (5.0 g, 18.55 mmol, 1.0 eq), (lS,2S)- Nl,N2- dimethylcyclohexane-l, 2-diamine (0.59 mL 3.71 mmol, 0.2 eq), Sodium ascorbate (368 mg, 1.86 mmol, 0.1 eq), Copper Iodide (530 mg, 2.78 mmol, 0.15 eq), Sodium azide (2.41 g, 37.1 mmol, 2.0 eq) , Et3N (3.11 mL, 22.26 mmol, 1.2 eq) and 2-(prop-2-yn-l-yloxy)tetrahydro- 2 /-pyran (2.6 g, 18.55 mmol, 1.0 eq) in Methanol (50 mL) and water (12 mL) were purged with Nitrogen for 5 minutes and heated to 55 C for over night. The reaction mixture was cooled to room temperature and filtered through 413 filter paper. Celite was added and the solvent was removed under reduced pressure and the residue was purified over silica gel (120 g) using dichloromethane/(methanol containing 12 % (v/v) aqueous ammonium hydroxide) as mobile phase. The concentration of (methanol containing 12 % (v/v) aqueous ammonium hydroxide) was gradually increased from 0 % to 6.25 % to afford (4-(4-(((tctrahydro-2/7-pyran-2- yljoxyjmcthyl)- 1 H- 1 ,2,3-triazol- 1 -yljphcnyljmcthanaminc (15, 3.54 g, 66%) as a white solid. LCMS m/z: [M + H]+ Calcd for C15H20N4O2 289.2; Found 289.2.

The synthetic route of 59528-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGILON THERAPEUTICS, INC.; SMITH, Devyn, McKinley; PERITT, David; VEISEH, Omid; HEIDEBRECHT, Richard; MILLER, Robert, James; (173 pag.)WO2019/195056; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 35944-64-0, 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. 35944-64-0, name is 3-Iodo-4-methylaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-Chloroisonicotinic acid (3.3g, 21mmol), HATU (8.75g, 23mmol), diisopropylethyl amine (10. 9ml, 63mmol) and 3-iodo-4-methylaniline (5. 00g, 21mmol) in dimethylformamide (50ml) were heated under nitrogen for 16 hours. The reaction was cooled, solvent removed in vacuo and the residue taken up in dichloromethane (150ml). The organic solution was washed with water (3xlOOml) and brine (100ml), dried over magnesium sulfate, filtered and solvent removed in vacuo. The residue was purified by column chromatography (40: 60 ethyl acetate: cyclohexane) to give 2-chloro-N- (3-iodo-4- methylphenyl) -isonicotinamide as a white solid (7. 00g, 18. 8mmol). LCMS: retention time 3.59 min Mu373. NMR: 8H [2H6]-DMSO 10.52 (1H, s), 8.62 (1H, d), 8.29 (1H, d), 7.99 (1H, b), 7.87 (1H, dd), 7.70 (1H, dd), 7.34 (1H, d), 2.36 (3H, s).

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, 3-Iodo-4-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2003/93248; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 52807-27-9,Some common heterocyclic compound, 52807-27-9, name is 4-Chloro-2-iodoanisole, molecular formula is C7H6ClIO, 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.

A solution of 4-chloro-2-iodo-1-methoxybenzene (500mg, 1.86mmol), the compound of preparation 28, (316mg, 1.86mmol), copper iodide (18mg, 0.09mmol), potassium carbonate (515mg, 3.72mmol), and ethylene glycol (208muL, 3.72mmol) in 2-propanol (5mL) was heated at 80 0C for 24h. The mixture was cooled to rt and the solvent was removed in vacuo. The residue was partitioned between EtOAc (2OmL) and water (2OmL). The phases were separated and the organic phase was dried over magnesium sulfate and the solvent was removed in vacuo to give the crude residue. Purification by column chromatography on silica gel using pentane:ethyl acetate (100:0-90:10) as eluent afforded the desired product as a white solid, 321 mg (56%)1H NMR (400 MHz, CDCI3) delta 3.80 (3H, s), 6.90 (1 H, d), 7.20 (1 H, s), 7.36 (1 H, m), 7.40 (3H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-2-iodoanisole, its application will become more common.

Reference:
Patent; PFIZER LIMITED; WO2006/67587; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde, molecular formula is C7H4BrIO, 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. name: 5-Bromo-2-iodobenzaldehyde

EXAMPLE 112b Preparation of intermediate 1-(2-iodo-5-bromo-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene To dry tetrahydrofuran (120 mL) was added a solution of LiHMDS (42 mmol, 42 ml) in THF under argon at room temperature, followed by the addition of 5-bromo-2-iodo-benzaldehyde (13 g, 42 mmol). After the mixture was stirred at room temperature for 0.5 h, trimethylsilyl chloride (5.32 mL, 42 mmol) was added dropwise. Then the temperature of the mixture was lowered to 0 C. on a cooling ice bath. To this mixture was added triethylamine (7.6 mL, 54.4 mmol) in one portion, followed by the dropwise addition of a solution of acetyl chloride (3.9 mL, 54.4 mmol) in diethyl ether (200 mL). The cooling bath was removed, and the mixture was stirred at room temperature for 1 h. The mixture was quickly filtered on celite under nitrogen, and filtrate was concentrated under reduced pressure to give the title compound as a yellow gum and used for the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 689291-89-2, its application will become more common.

Reference:
Patent; Ding, Qingjie; Jiang, Nan; Yang, Song; Zhang, Jing; Zhang, Zhuming; US2009/156610; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com