Tag: M.W=100-200

Synthetic Route of 202925-07-3, These common heterocyclic compound, 202925-07-3, name is 2-Chloro-1-fluoro-4-methoxybenzene, 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 solution of 3-chloro-4-fluoroanisole (28.5 g, 178 mmol) in i-butyl methyl ether (200 mL, dried over anhydrous MgS04) at -78 C was added 2.5 M n-butyl lithium in hexanes (107 mL, 267.5 mmol). After 3 h, methyl formate (18.76 mL) was added drop-wise while keeping the temperature below -60 C. The reaction mixture was quenched with sat. aq. ammonium chloride (250 mL) after 45 minutes and the organic layer was separated. The aq. layer was extracted with ethyl acetate (2×100 mL) and the combined organic layer was washed with water (200 mL) followed by brine, dried (Na2S04) and concentrated to give a residue which on trituration with hexanes gave solids. The solids were filtered, taken again in hexanes and heated over steam bath. It was cooled, the light yellow desired product filtered and air dried to give the title compound. 1H NMR (400 MHz, CDCI3): delta = 10.48 (d, J = 0.8 Hz, 1 H), 7.31 (dd, J = 9.4, 7.8 Hz, 1 H), 6.88 (dd, J = 7.8, 3.8 Hz, 1 H), 3.92 (s, 3H). 13C NMR (100.6 MHz, CDCI3, DEPT135): delta = 188.36 (+, JCF = 2.4 Hz), 158.01 (Cquart, JCF = 2.0 Hz), 152.73 (Cquart, JCF = 243.0 Hz), 122.87 (Cquart), 122.85 (Cquart, JCF = 18.4 Hz), 121 .01 (+, JCF = 24.5 Hz), 1 10.65 (+, JCF = 6.9 Hz), 56.57 (+).

The synthetic route of 202925-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI PHARMACEUTICALS, LLC; JIN, Meizhong; MULVIHILL, Mark, J.; STEINIG, Arno, G.; WANG, Jing; WO2012/158658; (2012); A1;,
Chloride – Wikipedia,
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Synthetic Route of 108-37-2, 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. 108-37-2, name is 1-Bromo-3-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of diisopropylamine (76 niL, 0.4 mol) in anhydrous THF (664 rnL) and n-hexane (220 rnL) was added 2.5 M n-BuLi (160 rnL, 0.4 mol) dropwise at -78 0C over 1 h. The mixture was stirred for 1 h at -78 0C and a solution of 1-bromo- 3-chlorobenzene (76 g, 0.4 mol) in anhydrous THF (300 mL) was added dropwise at – 78 0C. After stirring for an additional 1 h at the same temperature, a solution of iodine (101 g, 0.4 mol) in anhydrous THF (400 mL) was added dropwise at -78 0C. The temperature was raised from -78 0C to rt during 2 h. After stirring for 18 h at rt, the mixture was concentrated in vacuo to give the crude product (120 g) which was distilled under reduced pressure to give l-bromo-3-fluoro-2-iodobenzene (115 g, 91%). 1H NMR (400MHz, CDCl3): 7.12-7.18 (t, IH), 7.35-7.41 (dd, IH), 7.49-7.54 (dd, IH); MS (E/Z): 317 (M+H+)

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-chlorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; VITAE PHARMACEUTICALS, INC.; WO2008/124577; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 452-73-3, 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. 452-73-3 name is 2-Chloro-4-fluoro-1-methylbenzene, 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.

EXAMPLE 1 Preparation of 2-chloro-4-fluorobenzyl bromide A solution of bromine (7.10 ml) in carbon tetrachloride (70 ml) was added slowly over a period of 3 hours to a solution of 2-chloro-4-fluorotoluene (20.0 g) in carbon tetrachloride (80 ml) maintained at the reflux temperature and irradiated by light from a tungsten lamp (200 watt). After the addition was completed the mixture was heated at the reflux temperature with irradiation until the colour had been discharged (ca.1 hour). The solvent was then removed by evaporation under reduced pressure and the residual oil distilled to yield 2-chloro-4-fluorobenzyl bromide (80% pure, 18.0 g) b.p. 110-120 C./15 mm Hg.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-4-fluoro-1-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; Imperial Chemical Industries PLC; US4567199; (1986); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 4535-90-4, These common heterocyclic compound, 4535-90-4, name is 2-Chloro-N-methylethanamine hydrochloride, 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 intermediate 33 (0.56 g; 1.46 mmol), tetrabutylammonium bromide (0.12 g; 0.37 mmol) and KOH (1.23 g; 21.9 mmol) in 2-methyltetrahydrofuran (8.5 mL) and water (1 mL) was heated at 50C for 1 hour. Methylaminoethyl chloride hydrochloride (0.34 g; 2.63 mmol) was added and the mixture was heated at 50C overnight. Water (200 mL) was added and the mixture was extracted with DCM (3 x 150 mL). The combined organic layers were dried over Na2S04, filtered and concentrated. The residue was purified by column chromatography over silica gel (eluent: DCM/MeOH 98/2 to 85/15). The fractions containing the product were collected and concentrated to afford after trituration in Et20 and drying under vacuum to give 0.408 g of the expected compound. This solid was purified by achiral SFC on (AMINO thetamuiotatauiota 150×21.2mm; mobile phase: 0.3% isopropylamine, 75% C02, 25% MeOH) to give 308 mg of an intermediate residue which was crystallized from Et20 to afford 256 mg (40%) of compound 30 . MP: 120C (gum) (Kofler).

The synthetic route of 4535-90-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; ANGIBAUD, Patrick Rene; OBRINGER, Michel; MARIN, Julien Jeremie Joseph; JEANTY, Matthieu; WO2013/61077; (2013); A1;,
Chloride – Wikipedia,
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Reference of 108-70-3, A common heterocyclic compound, 108-70-3, name is 1,3,5-Trichlorobenzene, molecular formula is C6H3Cl3, 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 50 mL 3 neck round bottom flask was oven dried, cooled under nitrogen, and char- ged with 14.50 g of xylenes. The flask was then charged with 1,3, 5-TRICHLOROBENZENE (9.760g, 53.49 MMOL), benzophenone imine (7.620 g, 42.04 MMOL), (dba) 3PD2 CATALYST (0.023 g, 0.03 mmol in 2 g xylene), dppf ligand (0.042 g, 0.08 MMOL IN 2 G XYLENE) and sodium t-butoxid (5.550 g, 57.70 mmol). The reaction mixture was heated to reflux (136 C) for 3 hours and then cooled to room temperature. The aromatic imine intermediate was then hydrolyzed with 22 ML OF 2 N HCI (aq) at 70 C for 45 minutes. The hydrochloride salt of dichloroaniline precipitated out of solution when cooled to room temperature. The crude hydrochloride salt was collected by filtration using a buchner funnel and then washed with methyl-tert. butyl ether. The DICHLOROANALINE SALT was then added to 30 mL of METHYL-TERT. BUTYL ether and pH adjusted to 12 using 50% NaOH. The methyl-tert. butyl ether phase was collected and then stripped under va- cuum to give 3, 5-DICHLOROANILINE in 86 % yield.

The synthetic route of 108-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF AKTIENGESELLSCHAFT; WO2004/54961; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-(2-Chloroethyl)azepane hydrochloride

To a solution of 1,1-bis(4-hydroxyphenyl)-2,2-diphenylethene (27.2 mg, 74.6 mumol) in DMF (0.75 mL) at 0 ¡ãC was added 60percent sodium hydride (dispersion in paraffin liquid, 23.9 mg, 0.598 mmol). The reaction mixture was stirred for 15 min at 50 ¡ãC and then N-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (48.8 mg, 0.246 mmol) was added in portions at room temperature. After the reaction mixture had been stirred for 1 h at 50 ¡ãC, saturated aqueous ammonium chloride was added at 0 ¡ãC. The mixture was extracted with dichloromethane and the organic layer was dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by thin layer chromatography on silica (eluant; ammoniacal chloroform/methanol = 30/1) to afford RID-F-S*14 (compound 10) (37.9 mg, 83percent) as a brown oil

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 26487-67-2.

Reference:
Article; Hasegawa, Makoto; Yasuda, Yukari; Tanaka, Makoto; Nakata, Kenya; Umeda, Eri; Wang, Yanwen; Watanabe, Chihiro; Uetake, Shoko; Kunoh, Tatsuki; Shionyu, Masafumi; Sasaki, Ryuzo; Shiina, Isamu; Mizukami, Tamio; European Journal of Medicinal Chemistry; vol. 71; (2014); p. 290 – 305;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2687-12-9, A common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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.

Specifically, a 200 mL flask containing 15.3 g (0.1mol) of compound lb and 25 g (0.15 mol) of triethyl phos-phite was stirred for 8 hours at 180 C.Next, afier cooling the flask to room temperature, excess triethyl phosphite was evaporated under reduced pressure to yield 22 g (percentage yield: approximately 87%) ofthe compound 3b (white liquid).

The synthetic route of 2687-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYOCERA Document Solutions Inc.; OKADA, Hideki; SUGAI, Fumio; KOJIMA, Kensuke; (23 pag.)US2016/152552; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, 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 2533-69-9, Product Details of 2533-69-9

A solution of 5,6-difluorobenzene-1,2-diamine (1.76 g, 12.2 mmol) in acetic acid (70 ml) was treated with methyl-2,2,2-trichloroacetimidate (1.5 ml, 12.2 mmol) and the resulting solution left to stir at room temperature for 16 hours. The solvent was removed in vacuo and the residue was dissolved in methanol (100 ml) and heated to reflux for 4 hours. The solvent was removed in vacuo and the residue partitioned between saturated aqueous sodium bicarbonate (100 ml) and ethyl actetae (100 ml). The organic phase was separated, dried (sodium sulphate) and reduced in vacuo. Purification by flash column chromatography on silica gel eluting with pentane:ethyl acetate (90:10 changing to 50:50, by volume) gave the title compound as a yellow solid (963 mg).

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; Lane, Charlotte Alice Louise; Price, David Anthony; US2006/111416; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 367-22-6, name is 4-Chloro-3-fluoroaniline, A new synthetic method of this compound is introduced below., Safety of 4-Chloro-3-fluoroaniline

Into a 500-mL round-bottom flask, was placed 4-chloro-3-fluorobenzenamine (5.08 g, 34.9 mmol), ACN (200 mL) and NBS (18.69 g, 105.0 mmol). The resulting solution was stirred for 12 h at RT and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:200 to 1:100). This resulted in 9.7 g (92%) of the title compound as a light yellow solid. MS-ESI: 303.8, 305.8, 301.8 (M+1).

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; IFM THERAPEUTICS, INC; GLICK, Gary; GHOSH, Shomir; ROUSH, William R.; (328 pag.)WO2017/184624; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 367-21-5,Some common heterocyclic compound, 367-21-5, name is 3-Chloro-4-fluoroaniline, molecular formula is C6H5ClFN, 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 solution of 3-chloro-4-fluoroaniline (5.82 g, 0.04 mol) in CH2Cl2(150 mL), N-bromosuccinimide (7.12 g, 0.04 mol) was added in portions at 0C under stirring. Upon completion of the addition, the resultant was stirred for 30 minutes and filtered. The filtrate was concentrated and purified by silica gel column chromatography to give 2-bromo-5-chloro-4-fluoroaniline (6.16 g, 69% yield). 1H-NMR (400 MHz, CDCl3):delta = 7.234 (d, J = 8.4 Hz, 1H), 6.788 (d, J = 6.4 Hz, 1H), 3.982 (br, 2H). MS m/z [ESI]: 225.9 [M+1].

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

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; XIAO, Dengming; XU, Xinhe; LIU, Xijie; HU, Yuandong; YU, Honghao; LIU, Zhihua; PENG, Yong; SUN, Yinghui; LUO, Hong; KONG, Fansheng; HAN, Yongxin; SUN, Jian; EP2952510; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics