Author: Jessica.F

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. 31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, A new synthetic method of this compound is introduced below., name: 4-Iodo-1,2-dimethylbenzene

(37-1) Synthesis of 3-(3,4-dimethylphenyl)-2-propyne-1-ol (compound 37-1) [Show Image] A mixture of 1-iodo-3,4-dimethylbenzene (5.00 g), copper(I) iodide (82.1 mg), triphenylphosphine (283 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (446 mg), propargyl alcohol (1.40 ml), diisopropylethylamine (15.0 ml) and tetrahydrofuran (100 ml) was stirred at room temperature for 5 hr. The reaction mixture was added to brine, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=98:2 – 80:20) to give the object product (2.12 g) as a brown oil. 1H-NMR(CDCl3) delta (ppm): 1.64(1H, t, J=6.2Hz), 2.23(3H, s), 2.26(3H, s), 4.48(2H, d, J=6.0Hz), 7.07(1H, d, J=7.7Hz), 7.18(1H, d, J=7.7Hz), 7.22(1H, s).

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; Mitsubishi Tanabe Pharma Corporation; EP2168944; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 13421-00-6, name is 5-Chloro-2-iodobenzoic acid, A new synthetic method of this compound is introduced below., name: 5-Chloro-2-iodobenzoic acid

The 1-[2,8-dichloro-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-piperazine (melting point 120-122 C.) used as the starting material can be prepared from 5-chloro-2-iodo-benzoic acid and 4-chloro-phenol in the manner described in Example 1, via the following intermediates:

The synthetic route of 13421-00-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US4032525; (1977); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, molecular formula is C6H3Cl2I, 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. HPLC of Formula: C6H3Cl2I

General procedure: To 4-amino-l-(4-methoxybenzyl)-lH-imidazo[4,5-c]pyridine-2-thiol (103) (50 mg, 0.174 mmol) was added respective iodine (0.348 mmol), neocuproine hydrate (3.6 mg, 0.0174 mmol), Cul (3.3 mg, 0.0174 mmol), sodium tert-butoxide (25 mg, 0.261 mmol) and lastly DMF (5 mL) and the reaction mixture was stirred at 1 10°C for 24 hours. Then, the solvent was removed under reduced pressure and the crude product was purified by preparatory TLC (CH2Cl2:MeOH-NH3 (7N), 10: 1) to afford desired compounds 104a-c. [0457] 2-((3,5-dichlorophenyl)thio)-l-(4-methoxybenzyl)-lH-imidazo[4,5-c]pyridin-4-amine (104a). Obtained as pale yellow solid 39percent yield. LCMS found m/z 430.97 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3032-81-3, its application will become more common.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; CHIOSIS, Gabriela; YAN, Pengrong; PATEL, Pallav; PATEL, Hardik J.; TALDONE, Tony; YANG, Chenghua; SUN, Weilin; OCHIANA, Stefan; WO2015/23976; (2015); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 4028-63-1, name is 2,4,6-Trimethyliodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 4028-63-1

General procedure: To a stirred solution of aryl halide (1.2mmol) and [Pd(pp3S4)(dba)] (1mol percent) in isopropanol (2.5ml) was added nitrogen/oxygen nucleophile (1mmol) followed by Cs2CO3 (2mol percent) in the atmosphere of air. The mixture was heated to 80°C and the progress of the reaction was monitored by TLC. After completion, the solvent was evaporated through rotavapour and the crude mixture was washed with dichloromethane-H2O and the organic phase was separated and dried over Na2SO4. The dichloromethane was evaporated followed by flash column purification on silica gel of the crude to obtain the pure products. The products were characterized using 1H, 13C NMR spectroscopy and GC?MS spectroscopy. The characterization data were in good agreement with those described in the literature.

The synthetic route of 4028-63-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Majumder, Arpi; Gupta, Ragini; Mandal, Mrinmay; Babu, Madhu; Chakraborty, Debashis; Journal of Organometallic Chemistry; vol. 781; (2015); p. 23 – 34;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 31827-94-8, The chemical industry reduces the impact on the environment during synthesis 31827-94-8, name is 2-Bromo-1-(4-iodophenyl)ethanone, I believe this compound will play a more active role in future production and life.

To a solution of 4-iodoacetophcnonc 4.9 ( 1 O g, 40.6 mmol) in dioxanc ( 100 mL) was added bromine (2.18 mL, 42.7 mmol) dropwise at 0 C. The reaction mixture was stirred for 30 minutes. The resulting solution was concentrated. The residue was dissolved in dichloromethane (200 mL) and was washed with satd. NaHCO3, H2O and brine, dried over Na2SO4, and concentrated to give 4.10. To a solution of 4.10 in DMF ( 100 mL) were added potassium carbonate ( 16.8 g, 122 rnmol) and /ert-butylcarbamidine hydrochloride 4.11 ( 1 1.1 g, 81.2 mmol). After stirring overnight, the reaction mixture was filtered and the filtrate was concentrated. The resulting residue was purified on silica gel using a mixture of hexanes and ethyl acetate to give 4.12 (8.1 g, 61%). LRMS (M+Na+) m/z 327.0.

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, 2-Bromo-1-(4-iodophenyl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CYTOKINETICS, INC.; SMITHKLINE BEECHAM CORPORATION; WO2007/56143; (2007); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 69113-59-3, A common heterocyclic compound, 69113-59-3, name is 3-Iodobenzonitrile, molecular formula is C7H4IN, 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.

To a 500 mL 3-neck round bottom flask was added aniline (3.13 g, 33.6 mmol) and 150 mL of toluene. The solution was cooled in an ice bath under nitrogen. Next trimethylaluminum solution in toluene was added dropwise via dropping funnel (2.0 M, 23.5 mL, 47.0 mmol) and the reaction mixture was stirred at room temperature for 2 h. Next 3-iodobenzonitrile (10 g, 44 mmol) in 50 mL of toluene was added and the reaction mixture was heated to 70 C overnight under nitrogen. The reaction mixture was cooled in an ice bath and then poured onto a stirring slurry of silica gel in 2: 1dichloromethane/methanol. The silica gel was filtered off and washed with dichloromethane and methanol. The filtrate was evaporated leaving a solid which was triturated with hexane, filtered, and washed with more hexane and dried (7.84 g, 73%).

The synthetic route of 69113-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; XIA, Chuanjin; YEAGER, Walter; LI, David Zenan; FIORDELISIO, James; MA, Bin; ELSHENAWY, Zeinab; LAYEK, Suman; BARRON, Edward; KOTTAS, Gregg; BROOKS, Jason; WO2012/116231; (2012); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 199786-58-8, These common heterocyclic compound, 199786-58-8, name is (5-Bromo-2-iodophenyl)methanol, 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.

Example 15C 5-Bromo-2-iodobenzaldehyde A solution of oxalyl chloride (1.53 g, 0.012 mol) in CH2Cl2 (15 mL) was cooled to -70 C., and DMSO (1.41 g, 0.018 mol) in CH2Cl2 (15 mL) was added at -65 to -70 C. The mixture was stirred under nitrogen for 10 minutes at -70 C. and then treated with the product from Example 15B (2.35 g, 7.5 mmol) in 60 mL CH2Cl2. The slurry was stirred at -65 C. for 15 minutes and treated with triethylamine (3.8 g, 0.037 mol). The mixture was allowed to warm to -10 C. over 1 hour. The mixture was treated with 20 mL of water and allowed to warm to room temperature. The organic layer was separated and concentrated to provide the title compound. 1H NMR (CDCl3, 400 MHz) delta 9.97. (s, 1H), 7.97 (d, J=4 Hz, 1H), 7.79 (d, J=8 Hz, 1H), 7.40 (dd, J=4, 8 Hz, 1H). MS (DCl/NH3) [M+NH4]+ at 328.

The synthetic route of 199786-58-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Altenbach, Robert J.; Black, Lawrence A.; Chang, Sou-Jen; Cowart, Marlon D.; Faghih, Ramin; Gfesser, Gregory A.; Ku, Yi-Yin; Liu, Huaqing; Lukin, Kirill A.; Nersesian, Diana L.; Pu, Yu-ming; Curtis, Michael P.; US2005/272736; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 98-61-3, These common heterocyclic compound, 98-61-3, name is 4-Iodobenzenesulfonyl chloride, 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.

A solution of (2-methylpropyl)amine (121 mg,1.65mmol) and triethylamine (0.35ml, 2.47mmol) in DCM (10ml) was treated with 4-iodobenzenesulfonyl chloride (500mg,1.65mmol) by dropwise addition over 10 minutes with stirring under argon.The reaction mixture was stirred at room temperature for 16 hr. Then the reaction mixture was washed with water (10ml), separated the organic layer, dried with sodium sulphate.Solvent was removed by rotary evaporation to give the title compound as a white solid (517mg, 92%).LC/Mass Spec (ES): Found 340 (ES+), retention time 3.14mins. C10H14INO2S requires339. 1H-NMR (400MHz, CDCI3): 0.88 (6H, m), 1.72 (1 H, m), 2.78 (2H, m), 4.41 (1 H, m)7.56 (2H, m), 7.88 (2H, m).

The synthetic route of 98-61-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/107539; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

1094759-93-9, name is 4-Chloro-5-fluoro-2-iodoaniline, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 4-Chloro-5-fluoro-2-iodoaniline

A solution of 4-chloro-5-fluoro-2-iodo-phenylamine (2.5 g, 9.21 mmol) and copper (I) cyanide (1.65 g, 18.4 mmol) in DMA (45 ml) was heated to 130C overnight. Most of the DMA was removed under reduced pressure and the remaining residue was diluted with EtOAc and dichloromethane. The slurry was filtered and the filter cake was washed with dichloromethane and EtOAc. The filtrate was concentrated and the remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 98:2 – 85: 15) to afford the title compound (1232 mg, 78%) as light red solid. MS (ESI): 169.2 (M-H)~.

The synthetic route of 1094759-93-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CECCARELLI, Simona M.; CONTE, Aurelia; KUEHNE, Holger; KUHN, Bernd; NEIDHART, Werner; OBST SANDER, Ulrike; RUDOLPH, Markus; WO2013/64465; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 2265-91-0, 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. 2265-91-0 name is 1,3-Difluoro-5-iodobenzene, 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.

To a flask containing a mixture of 1,3-difluoro-5-iodo-benzene(900 mg, 3.75 mmol) and 1,4-dioxa-8-azaspiro[4.5]decane (644 mg, 4.5 mmol) in dioxane (20 mL) was added t-BuONa(720 mg, 7.5 mmol), Pd2(dba)3 (174 mg, 0.19 mmol) and Sphos (156 mg, 0.38 mmol) successively under N2. Then the resulting mixture was heated to 100 C and stuffed overnight. After being cooled to rt, the resulting reaction mixture was diluted with H20 (20 mL) and extracted with EA (50 mL) for three times. The combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give crude 8-(3,5- difluorophenyl)-1,4-dioxa-8-azaspiro[4.5]decane (900 mg), which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Difluoro-5-iodobenzene, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com