Tag: M.W=200-300

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. 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, A new synthetic method of this compound is introduced below., Recommanded Product: 2,4-Difluorobenzene-1-sulfonyl chloride

A mixture of 1.50 g (5.8 mmol) E-3, 3.08 mL (23.2 mmol) 2,4-difluoro-benzenesulfonyl chloride, 1.9 mL (24.4 mmol) pyridine and 40 mL DCM is stirred at RT over night. The reaction mixture is concentrated under reduced pressure and the residue is purified with RP-chromatograpy. Yield: 0.71 g (28%).

The synthetic route of 13918-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WUNBERG, Tobias; KRAEMER, Oliver; van der VEEN, Lars; US2013/23533; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 157590-59-5, The chemical industry reduces the impact on the environment during synthesis 157590-59-5, name is 4-Chloro-5-(trifluoromethyl)benzene-1,2-diamine, I believe this compound will play a more active role in future production and life.

To a solution of Intermediate II (300 mg, 0.887 mmol) and triethylamine (500 mg, 5 mmol) in DMF (5 mL) was added HATU (370 mg, 0.97 mmol) at 0 C. After the mixture was stirred for 15 min, 4-chloro-5-(trifluoromethyl)benzene-l,2-diamine (228 mg, 1.09 mmol) in DMF (1 mL) was added to the reaction. The mixture was allowed to warm to room temperature and stirred for 20hrs. The reaction was diluted with water (50 mL) and the white solid was precipitated. The mixture was filtered and the solid was dried enough under reduced pressure. The solid was dissolved in acetic acid (5 mL) and the mixture was stirred at 85 C for 5hrs. Solvent was removed. The residue was purified by silica gel chromatography (eluted with DCM:MeOH = 50: 1~ 20: 1) to give the title compound (205 mg, 45%) as a light yellow solid. 1H- NMR (400 MHz, DMSO-ifc) delta 10.48 (s, 1H), 7.96 (d, J = 4.1 Hz, 2H), 7.82 (s, 1H), 7.37 (d, J = 2.6 Hz, 1H), 7.07 (d, J = 8.7 Hz, 1H), 7.01 (dd, J = 8.7, 2.6 Hz, 1H), 6.26 (d, J = 5.8 Hz, 1H), 5.42 (d, J = 5.3 Hz, 1H), 3.57 – 3.51 (m, 1H), 2.93 (t, J = 7.7 Hz, 2H), 2.58 – 2.50 (m, 2H), 1.98 (d, J = 2.1 Hz, 1H) ppm. MS: M/e 513 (M+l)+.

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-Chloro-5-(trifluoromethyl)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BEIGENE, LTD.; ZHOU, Changyou; WANG, Shaohui; ZHANG, Guoliang; WO2013/97224; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, belongs to chlorides-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 1996-30-1, SDS of cas: 1996-30-1

A solution of iso-propylmagnesium chloride in tetrahydrofuran (2M, 106. 6ml) was added dropwise over 15 minutes to a stirred solutionof 2-bromo-4-chloro-1-fluorobenzene (42. 5g) in anhydrous tetrahydrofuran(250ml) at0 C under nitrogen. After a further 15 minutes, a solution ofl-oxa-6-azaspiro [2.5] octane-6-carboxylic acid,1, 1-dimethylethyl ester (43.2g) in anhydrous tetrahydrofuran(50ml) was added followed by copper (I) bromide dimethyl sulphide complex (0.4g). The mixture was stirred at40 C for 18 hours, cooled to20 C, diluted with water(300ml) and extracted with withtert.-butyl methyl ether (2 x300ml). Organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. The residual oil was dissolved in 1,2-dimethoxypropane(200ml). Potassium tert-butoxide (22.8g) was added and the mixture stirred at40 C for 16 hours then at50 C for 24 hours. Further potassium tert.- butoxide (5.7g) was added and stirring continued at50 C for 2 hours then at55 C for 4 hours. Water (500ml) was added and the mixture extracted with tert.-butyl methyl ether (2 x300ml). Organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give the sub-title compound (47.45g, 67 %) as an oil. ‘H-NMR (400 MHz,CDC13) :8 1.47 (9h, s), 1.67 (2H, td), 1.85-1. 93 (2H, m), 2.94 (2H, s), 3.39 (2H, td), 3.65-3. 80 (2H,m), 6.67(1H, d), 7.06(1H, d), 7.10(1H, s).

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

Reference:
Patent; ASTRAZENECA AB?; WO2005/49620; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 61881-19-4,Some common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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.

10249] To a solution of 6-(6?-azidohexyl)-2,3,4-tri-O-ben- zyl-a/3-D-galactopyranose 18 (400 mg, 0.70 mmol) in CH2C12 (7 mE) was added cesium carbonate (340 mg, 1.04 mmol). To the mixture was added 2,2,2-trifluoro-N-pheny- lacetimidoyl chloride 24 (216 mg, 1.04 mmol) and the reaction mixture was stirred at r.t. for 3.5 h after which it was filtered over celite and washed with CH2C12. The solvent was removed in vacuo and the crude product was purified by flash column chromatography on silica gel (gradient hexanes/ EtOAc1 0:1 – 1:1) to yield the imidate 19 (490 mg, 94%) as a colorless oil. [a]Dt+60.8 (c0.4, CHC13); R1O.8O (Hexanes/EtOAc 2:1); IR (film) vm,x 3064, 2934, 2865, 2094, 1717, 1598, 1454, 1321, 1207, 1099, 1027, 910, 734, 696cm?; ?H NMR (400 MHz, CDC13) oe 7.45-6.60 (m, 20H),5.56 (s, 1H), 4.90 (d, J11.5 Hz, 1H), 4.75 (s, J1.5 Hz, 2H),4.68 (s, J12.4 Hz, 2H), 4.58 (d, J11.6 Hz, 1H), 4.00 (t,J8.7 Hz, 1H), 3.84 (d, J2.4 Hz, 1H), 3.58-3.39 (m, 4H),3.34 (dt, J9.3, 6.5 Hz, 1H), 3.23 (dt, J9.3, 6.5 Hz, 1H), 3.14(t, J6.9 Hz, 2H), 1.52-1.38 (m, 4H), 1.32-1.16 (m, 4H); ?3CNMR (101 MHz, CDC13) oe 138.6, 138.3, 138.2, 128.8, 128.6,128.5, 128.4, 128.4, 128.3, 128.0, 127.9, 127.8, 127.7, 124.3,119.4,82.3,78.3,77.4,77.2,76.8,75.7,74.9,74.6,73.4,73.2,71.4, 68.7, 51.5, 29.7, 28.9, 26.7, 25.8; HR ESI Calcd forC41H45F3N406 [M+Na]: 769.3183. found: 769.3239.

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

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; UNIVERSITAeTSSPITAL BASEL; Seeberger, Peter H.; Stallforth, Pierre; De Libero, Gennaro; Cavallari, Marco; US2015/238597; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 61881-19-4, A common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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 mixture of 12 (1.35 g, 1.16 mmol), (N-phenyl)-2,2,2-trifluoroacetoimidoyl chloride (482 mg, 2.32 mmol), andK2CO3 (802 mg, 5.80 mmol) in acetone (23.2 mL) was stirred for 1 h at room temperature. The reaction mixture was filtered through Celite, and concentrated. The crude product was purified by gelpermeation chromatography [S-X3, toluene-EtOAc (75:25)] and silica gel column chromatography with hexane-EtOAc (71:29) to give the title product 13 (1.31 g, 85%). [alpha]D -0.7 (c 1.4, CHCl3);1H-NMR (500 MHz, CDCl3) delta7.38-7.08 (m, 23H, Ar), 6.75-6.71 (m, 3H, Ar, NH), 6.32 (br, 1H, H-1GlcN),5.88-5.80 (m, 1H, H2C=CHCH2), 5.31-5.21 (m, 5H, H2C=CHCH2, H-1Fuc, H-2Fuc, H-3Fuc, H-4Fuc),5.14 (dd, 1H, Jtrans = 10.5 Hz, Jgem = 1.4 Hz, H2C=CHCH2), 4.95 (dd, 1H, J4,5 = 10.5 Hz, J5,6 = 6.4 Hz,H-5Fuc), 4.84 (d, 1H, Jgem = 11.9 Hz, PhCH2), 4.73 (d, 1H, Jgem = 11.4 Hz, PhCH2), 4.64-4.49 (m, 7H,PhCH2 5, H-2GlcN, H-1Gal), 4.44 (d, 1H, Jgem = 11.6 Hz, PhCH2), 4.16 (t, 1H, J2,3 = J3,4 = 9.2 Hz,H-3GlcN), 4.10-4.05 (m, 3H, H2C=CHCH2 2, H-4GlcN), 3.87-3.81 (m, 3H, H-4Gal, H-6aGal, H-5GlcN),3.70 (dd, 1H, J5,6b = 7.5 Hz, Jgem = 9.2 Hz, H-6bGal), 3.62-3.56 (m, 3H, H-2Gal, H-6aGlcN, H-6bGlcN),3.46-3.44 (m, 1H, H-5Gal), 3.24 (dd, 1H, J2,3 = 9.7 Hz, J3,4 = 2.7 Hz, H-3Gal), 2.14 (s, 3H, Ac), 2.02 (s, 3H,Ac), 2.00 (s, 3H, Ac), 0.78 (d, 3 H, H-6Fuc); 13C-NMR (125 MHz,CDCl3) delta 170.4, 120.2, 169.5, 161.2, 142.9, 138.7, 138.4, 138.2, 137.5, 134.9, 129.2, 129.0, 128.8, 128.5, 128.4,128.3, 128.2, 128.1, 128.0, 127.8, 127.8, 127.7, 127.6, 127.3, 124.6, 119.3, 116.6, 103.8, 95.9, 92.4, 81.9, 78.5, 77.6,74.9, 74.8, 74.2, 73.7, 73.7, 73.3, 73.2, 72.2, 71.9, 71.7, 71.6, 68.7, 68.1, 68.0, 66.7, 64.8, 54.7, 20.8, 20.8, 20.7, 15.4.HRMS (ESI) m/z: found [M + Na]+ 1351.3539, C65H70Cl3F3N2O18 calcd. for [M + Na]+ 1351.3539.

The synthetic route of 61881-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kobayashi, Daisuke; Ueki, Akiharu; Yamaji, Tomoya; Nagao, Kazuya; Imamura, Akihiro; Ando, Hiromune; Kiso, Makoto; Ishida, Hideharu; Molecules; vol. 21; 5; (2016);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H3BrClF

To a mixture of 2-bromo-4-chloro-l-fluorobenzene (2 g, 9.55 mmol) and liT-pyrazole (0.618 g, 9.07 mmol) in DMF (20 mL) was added Cs2C03(6.22 g, 19.10 mmol). The reaction mixture was stirred at 90C for 1 hour. LCMS showed the reaction was completed. The reaction was cooled to 25C, diluted with EtOAc (30 mL) and water (30 mL). The aqueoUs layer was extracted with EtOAc (2 x 30 mL). The combined organic phase was dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica (0-10% EtOAc/petroleum ether) to give the title compound.

The synthetic route of 1996-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; DEBENHAM, John, S.; ZHU, Cheng; (64 pag.)WO2020/86416; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 873-38-1, name is 2-Bromo-4-chloroaniline, belongs to chlorides-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 873-38-1, category: chlorides-buliding-blocks

In a 20 mL microwave vial was added 2-bromo-4-chloroaniline (3 g, 14.53 mmol), 4,4,5,5 -tetramethyl-2-(tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1,3 ,2-dioxaborolane (5.53 g, 21.80 mmol), KOAc (3.66 g, 37.3 mmol), Pd(dppf)C12-CH2C12 adduct (0.32 g,0.44 mmol) and DMSO (9 mL). The resulting suspension was purged with N2, capped and heated at 80 C for 22 h. The reaction was cooled to rt. Water was added to dissolve the salts, then the reaction was filtered. The remaining solid was suspended in DCM and the insoluble solid was filtered. The filtrate was concentrated and then purified by normal phase chromatography to give 4-chloro-2-(tetramethyl- 1,3 ,2-dioxaborolan-2-yl)aniline (3.15 g, 86% yield) as a white solid. MS(ESI) m/z:172.3 (M-C6H,o+H). ?H NMR (400MHz, CDC13) oe 7.54 (d, J2.6 Hz, 1H), 7.13 (dd, J8.8, 2.6 Hz, 1H), 6.52 (d, J8.6 Hz, 1H), 4.72 (br. s., 2H), 1.34 (s, 12H).

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; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 210532-25-5, These common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl 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.

To a stirred suspension of TFA salt of 9-(3-amino-propyl)-6,7,8,9-tetrahydro-5H- carbazole-3-carboxylic acid methyl ester (0.2 g, 0.5 mmol), in 2 ml of dry CH2Cl2, NEt3 (0.208 ml, 1.5 mmol) was added at 0 C. After stirring for 5 min, 3,5-difluorobenzene sulfonylchloride (0.106 g, 0.5 mmol), in 1 ml of dry CH2Cl2 was added and the mixture was stirred for 3 hrs. The reaction mixture was diluted with CH2Cl2, washed sequentially with IN HCl (25 ml), H2O (25 ml) and sat. NaHCO3 (25 ml) solution. The organic layer was separated, dried over anhyd.MgSO4, solvents removed in vacuo and the crude was purified by column chromatography, using EtOAc/hexane as eluents, to obtain 0.14g of the product. 1H NMR 500 MHz CDCl3: 8.2, d, J = 1.4, IH, 7.8, dd, J = 1.6, 8.7, IH, 7.3-7.24, m, 2H, 7.15, d, J = 8.7, IH, 7.04-6.97, m, IH, 4.48, t, J = 5.9, IH, 4.1, t, J = 7, 2H, 3.92, s, 3H, 2.98, q, J = 6.6, 2H, 2.73, t, J = 6.2, 2H, 2.66, t, J = 5.9, 2H, 2.05-1.89, m, 4H, 1.88-1.82, m, 2H.

The synthetic route of 210532-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ITHERX PHARMACEUTICALS, INC.; WO2009/103022; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 14862-52-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 14862-52-3 as follows.

1,3-dibromo-5-chlorobenzene (100 g, 370 mmol) was dissolved in THF (2 L) in a nitrogen environment, phenylboronic acid (47.3 g, 388 mmol) and tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (1.5 g, 1.36 mmol) were added thereto, and the mixture was stirred. Potassium carbonate (K2CO3) (127 g, 925 mmol) saturated in water was added thereto, and the resulting mixture was heated and refluxed at 80 C. for 12 hours. When the reaction was complete, water was added to the reaction solution, the mixture was extracted with dichloromethane (DCM), and an extract therefrom was filtered and concentrated under a reduced pressure after removing moisture with anhydrous MgSO4. The obtained residue was separated and purified through flash column chromatography to obtain an intermediate I-6 (49 g, 50%). HRMS (70 eV, EI+): m/z calcd for C12H8BrCl: 265.9498, found 266 Elemental Analysis: C, 54%; H, 3%

According to the analysis of related databases, 14862-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMSUNG SDI CO., LTD.; KANG, Giwook; KIM, Younhwan; KIM, Youngkwon; KIM, Dongyeong; KIM, Hun; OH, Jaejin; CHO, Pyeongseok; YU, Eun Sun; (176 pag.)US2017/92873; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 201849-17-4, These common heterocyclic compound, 201849-17-4, name is 1-Bromo-2-chloro-5-fluoro-4-methylbenzene, 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 isopropyl magnesium chloride in THF (2.0 M; 27.2 mL) was added dropwise to a mixture of 1-bromo-2-chloro-5-fluoro-4-methylbenzene (8.10 g) and THF (55 mL) at -10 C. under an argon atmosphere, followed by stirring at -10 C. for 45 minutes. A mixture of iodine (18.4 g) and THF (26 mL) was added dropwise to the reaction mixture at -75 C., followed by stirring at -75 C. for 3 hours. A saturated aqueous Na2S2O3 solution was added to the reaction mixture at -75 C., followed by stirring at room temperature for 15 minutes. Saturated aqueous sodium bicarbonate was added to the reaction mixture at room temperature, followed by extraction with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and then concentrated under reduced pressure, thereby obtaining 1-chloro-4-fluoro-2-iodo-5-methylbenzene (9.71 g).

Statistics shows that 1-Bromo-2-chloro-5-fluoro-4-methylbenzene is playing an increasingly important role. we look forward to future research findings about 201849-17-4.

Reference:
Patent; ASTELLAS PHARMA INC.; ISHIHARA, Tsukasa; IKEGAI, Kazuhiro; KURIWAKI, Ikumi; HISAMICHI, Hiroyuki; TAKESHITA, Nobuaki; TAKEZAWA, Ryuichi; US2014/364421; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics