Iodides-buliding-blocks

82998-57-0,Some common heterocyclic compound, 82998-57-0, name is 3-Iodo-4-methylbenzoic acid, molecular formula is C8H7IO2, 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.

3-Iodo-4-methyl benzoic acid (200 mg, 0.763 mmol) and thionyl chloride (4.5 mL, 612 mmol) were heated to 80 C. in a round-bottom flask equipped with a reflux condenser for 1 hr. After cooling to room temperature, the reaction mixture was concentrated on the rotary evaporator and then high vacuum for 10 minutes. The residue was dissolved in CH2Cl2 -(7.6 mL), and then the flask was charged with triethylamine (0.21 mL, 1.53 mmol) and 4-fluoro-3-(trifluoromethyl)benzenamine (0.916 mmol, 0.118 mL). The reaction mixture was allowed to stir at room temperature for 4 hrs. Upon completion, the reaction mixture was concentrated in vacuo. The residue was purified by automated chromatography (100% CH2Cl2) to yield N-(4-fluoro-3-(trifluoromethyl)phenyl)-3-iodo-4-methylbenzamide. MS m/z=421 [M-2H]-, 422 [M-H]-. Calc’d for C15H10F4INO3: 423

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Iodo-4-methylbenzoic acid, its application will become more common.

Reference:
Patent; Amgen Inc.; US2007/54916; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

1643-29-4, 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. 1643-29-4 name is 3-(4-Iodophenyl)propanoic acid, 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.

In the l00mL hydrothermal synthesis reactor,Add sodium hydroxide (3 mmol), water (5 mL), stir and dissolve,Adding iodinePhenylpropionic acid(0.5 mmol), cuprous oxide (0.05 mmol),White lignan (0.05 mmol), the reaction was stirred at 100 C for 6 hours.After cooling, the pH was adjusted to 2 with dilute hydrochloric acid and extracted with ethyl acetate.The extract was concentrated and subjected to column chromatography to obtain p-hydroxyphenylpropionic acid, 65.6 mg.The yield was 79%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(4-Iodophenyl)propanoic acid, and friends who are interested can also refer to it.

Reference:
Patent; Shenyang Pharmaceutical University; Yunnan Tropical Crop Science Institute; Chen Guoliang; Wu Ying; Bao Xuefei; Li Guohua; Liang Xinjie; Jiang Shikuan; Zhou Qifan; Du Fangyu; (11 pag.)CN109970542; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, 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. 77317-55-6 name is Methyl 2-amino-5-iodobenzoate, 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: A mixture of substituted iodobenzene (2 mmol), (5-formylfuran-2-yl)boronic acid (420 mg, 3mmol, 1.5 equiv), Pd(Ph3P)2Cl2 (0.1 mmol, 0.05 equiv, 70 mg) and potassium carbonate (6 mmol,3 equiv, 828 mg) in dioxone/H2O (6 mL/2 mL) was stirred at 100 C under argon atmosphereuntil the starting material was consumed (typically 20 h). The reaction mixture was then diluted with 25 mL of saturated brine. The mixture was then extracted with EtOAc (25 mL ¡Á 2), and the organic layers were combined, dried over Na2SO4. The concentrated crude product was purifie dby column chromatography to afford c2a-e. The second step is the same as procedure A.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-5-iodobenzoate, and friends who are interested can also refer to it.

Reference:
Article; Liang, Dongdong; Robinson, Elizabeth; Hom, Kellie; Yu, Wenbo; Nguyen, Nam; Li, Yue; Zong, Qianshou; Wilks, Angela; Xue, Fengtian; Bioorganic and Medicinal Chemistry Letters; vol. 28; 6; (2018); p. 1024 – 1029;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding some certain compound to certain chemical reactions, such as: 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, 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 20555-91-3. 20555-91-3

General procedure: To a stirred solution of but-3-yn-2-amine (¡À) (Intermediate 2a) (5.00g, 72.34mmol) in dichloromethane (100 mL), tert-butyl 4-(chlorocarbonyl) piperazine-l-carboxylate (Intermediate 5) (17.90 g, 72.34mmol) and DIPEA (37.60 mL, 217 mmol) were added at RT. The reaction mixture, after being stirred at RT for 16 h, washed with saturated NaHC03 solution and brine. The dichloromethane layer was collected, dried and concentrated. The crude obtained was purified by Combiflash on silica gel (hexanes/ethyl acetate=65/35) to get the title compound (8.00 g, 39.4%). LCMS: m/z = 282.2 [M+H]+.

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 1,2-Dichloro-4-iodobenzene.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak V.; RAMACHANDRA, Muralidhara; SATYAM, Leena Khare; (139 pag.)WO2019/142126; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The chemical industry reduces the impact on the environment during synthesis 54811-38-0, name is 5-Iodo-2-methylbenzoic acid, I believe this compound will play a more active role in future production and life. 54811-38-0

To a solution of compound 6 (40.0 g, 0.153 mol) in MeOH (400 mL) was added dropwise a freshly prepared solution of SOCI2 (22 mL, 0.305 mol) in MeOH (400 mL) at O0C. The mixture was heated to reflux for 4 hours. TLC (petroleum ether: ethyl acetate = 10:1) showed the reaction was complete, then the mixture was concentrated in vacuo. The residue was desolved in ethyl acetate (800 mL) and washed with water (200 mLx2), saturated aqueous sodium carbonate (200 mLx2) and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give compound 7 as a yellow solid. 1H NMR (300 MHz, CDCI3): delta 8.21 (S, 1 H), 7.67-7.70 (dd, J = 9.0 Hz, 1 H), 6.97-6.99 (d, J = 6.0 Hz, 1 H), 3.88 (s, 3H), 2.53 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 54811-38-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; WO2006/117669; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

364-12-5, The chemical industry reduces the impact on the environment during synthesis 364-12-5, name is 5-Bromo-2-iodobenzotrifluoride, I believe this compound will play a more active role in future production and life.

(1) Synthesis of 1-[4-bromo-2-(trifluoromethyl)phenyl]cyclobutanol To a solution of 5-bromo-2-iodobenzotrifluoride (5.00 g) in dehydrated tetrahydrofuran (140 mL), n-butyl lithium (2.69 mol/L, solution in n-hexane, 5.30 mL) was added at -78C and the mixture was stirred at that temperature for 25 minutes. After adding a solution of cyclobutanone (999 mg) in tetrahydrofuran (5.00 mL), the mixture was brought to room temperature and stirred for 3 days. After adding a saturated aqueous solution of ammonium chloride under cooling with ice, two extractions were conducted with ethyl acetate. The combined organic layers were washed with water and thereafter dried over anhydrous magnesium sulfate. After removing the desiccant by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 98:2-80:20) to give 1-[4-bromo-2-(trifluoromethyl)phenyl]cyclobutanol as a pale yellow oil (3.00 g). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.71 – 1.88 (m, 1 H) 2.20 – 2.49 (m, 3 H) 2.52 – 2.70 (m, 2 H) 7.29 – 7.35 (m, 1 H) 7.62 – 7.69 (m, 1 H) 7.78 – 7.84 (m, 1 H). MS EI posi: 294[M]+.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-2-iodobenzotrifluoride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; TAKAYAMA, Tetsuo; SHIBATA, Tsuyoshi; SHIOZAWA, Fumiyasu; KAWABE, Kenichi; SHIMIZU, Yuki; HAMADA, Makoto; HIRATATE, Akira; TAKAHASHI, Masato; USHIYAMA, Fumihito; OI, Takahiro; SHIRASAKI, Yoshihisa; MATSUDA, Daisuke; KOIZUMI, Chie; KATO, Sota; EP2881384; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

455-13-0, Adding a certain compound to certain chemical reactions, such as: 455-13-0, name is 4-Iodobenzotrifluoride, 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 455-13-0.

General procedure: To a stirred solution of aryl halides (2.0 mmol) and thiourea (1.2 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 110 C for 15 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (20 mL) was added. The combined organic extracts were dried with anhydrous Na2SO4. The solvent and volatiles were completely removed under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 9:1) to afford the corresponding coupling product in excellent yields.Recycling of the catalyst:after the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (2.0 mL) was added and CuO was removed by centrifugation. After each cycle, the catalyst was recovered by simple centrifugation, washing with deionized water and ethyl acetate and then drying in vacuo. The recovered nano CuO was used directly in the next cycle.Data of representative examples:Dip-tolylsulfane (Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Bis(4-ethylphenyl)sulfane (Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Bis(3-nitrophenyl)sulfane (Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.4,4′-Thiodianiline (Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Dithiophen-3-ylsulfane (Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Dipyrimidin-5-ylsulfane (Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; found: C, 50.45; H, 3.13; N, 29.41; S, 16.81.Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; f…

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, 4-Iodobenzotrifluoride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Reddy, K. Harsha Vardhan; Reddy, V. Prakash; Shankar; Madhav; Anil Kumar; Nageswar; Tetrahedron Letters; vol. 52; 21; (2011); p. 2679 – 2682;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

1450754-38-7, These common heterocyclic compound, 1450754-38-7, name is 3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine, 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.

(g) Compound 6 (400 mg, 1.6 mmol, 1.0 eq), sodium azide (125 mg, 1.92 mmol, 1.2 eq) and DMF (4 ml) were added to a reaction flask, and the temperature was raised to 70 C, and the reaction was carried out for 5 hours in the dark;Quenched with water, extracted with ethyl acetate, dried and dried to give a crude200 mg of compound 7, yield: 76%.

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 1450754-38-7.

Reference:
Patent; Suzhouguangdian Biological Technology Co., Ltd.; Ni Runyan; Wang Wei; (8 pag.)CN109369532; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

83171-49-7, A common heterocyclic compound, 83171-49-7, name is 3-Chloro-5-iodoaniline, molecular formula is C6H5ClIN, 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: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.

The synthetic route of 83171-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zitko, Jan; Barbora, Servusova-Vanaskova; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Frantisek; Kunes, Jiri; Dolezal, Martin; Chemical Papers; vol. 70; 5; (2016); p. 649 – 657;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

444-29-1, 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. 444-29-1, name is 1-Iodo-2-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of [9-((1R,2R,4R,5R)-4-ethynyl-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl)purin-6-yl]cyclopentylamine (40 mg, 0.12 mmol), a compound of formula (5), in tetrahydrofuran (4 ml) under nitrogen was added catalytic amounts (3 mg) of dichlorobis(triphenylphosphine)palladium(II) and copper(II)iodide, followed by 1-iodo-2-trifluoromethylbenzene (0.25 ml, 0.3 mmol). Triethylamine (0.4 ml) was then added, and the mixture stirred for 15 minutes at room temperature. The solvent was removed under reduced pressure, and the residue was purified by preparative TLC, eluding with methanol:methylene chloride (6.5:1), to yield [9-((1R,2R,4R,5R)-7,7-dimethyl-4-{2-[2-(trifluoromethyl)-phenyl]ethynyl}-3,6,8-trioxabicyclo[3.3.0]oct-2-yl)purin-6-yl]cyclopentylamine, a compound of formula (6).

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:
Patent; Zablocki, Jeff; Palle, Venkata; Elzein, Elfatih; Li, Xiaofen; US2004/43960; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com