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. 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromo-2-chloro-1-fluorobenzene

A dry, argon-flushed Schienk-flask equipped with a magnetic stirrer and a septum was charged with 20 mL freshly titrated iPrMgClLiCI (1.24 M in THE, 1.0 equiv.) to which 3.8 mL of diisopropylamine (1.1 equiv.) was added dropwise at 25 00. The reaction mixture was stirred at this temperature until gasevolution was completed (ca. 48 h). The formed precipitate was dissolved with additional dry THE. The fresh solution of iPr2NMgCILiCI in THE was titrated at 25 00 with benzoic acid and 4- (phenylazo)diphenylamine as an indicator. A concentration of 0.59 M was obtained.To a solution of 4-bromo-2-chloro-1 -fluoro-benzene (0.209 g, 1 .00 mmol) in THE (1 mL) was added iPr2NMgCILiCI (0.59 M, 3.39 ml, 2.00 mmol) at 25 00 and the resulting mixture was stirred for 15 mm at25 c Hexachloro-2-propanone (0.397 g, 1 .50 mmol) was added at 0 00 and the mixture was stirred for15 mm. The resulting mixture was then quenched with sat. aq. NH4CI, extracted with ethyl acetate and dried over anhydrous Na2SO4. After filtration, the solvent was removed in vacuo. Quantitative GO measurement showed that the ratio between 5-bromo-1 ,3-dichloro-2-fluoro-benzene and regioisomer is about 12:1. Purification by flash column chromatography (Si02, i-hexane) furnished 5-bromo-1 ,3-dichloro-2-fluoro-benzene (0.190 g) as a colorless oil.

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; SYNGENTA PARTICIPATIONS AG; SMITS, Helmars; KNOCHEL, Paul; KLATT, Thomas; BECKER, Matthias; (18 pag.)WO2016/58895; (2016); A1;,
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These common heterocyclic compound, 2401-24-3, name is 2-Chloro-5-methoxyaniline, 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. name: 2-Chloro-5-methoxyaniline

3-bromo-6-methoxy-2-methylpyridine (Aldrich catalog No.758191-1G,0.3 g, 1.485 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl (0.053 g, 0.111 mmol), cesium carbonate (0.581 g, 1.782 mmol) and palladium (II) acetate (0.017 g, 0.074 mmol) were added to a microwave vial. Then, 2-chloro-5-methoxyaniline (Chemimpex catalog No.27675, 0.246 g, 1.559 mmol) was added. The solvent was degassed with argon twice. The reaction was heated on a heating block to 100 C. for 15 hours. The crude reaction mixture was cooled to room temperature and then filtered through celite. The celite was rinsed repeatedly with ethyl acetate to collect the crude product mixture. A reverse-phase column was run (water, acetonitrile) to give N-(2-chloro-5-methoxyphenyl)-6-methoxy-2-methylpyridin-3-amine (0.286 g, 69% yield). 1H NMR (CDCl3, 400 MHz) delta 7.42 (d, 1H, J=8.4 Hz), 7.20 (d, 1H, J=8.4 Hz), 6.60 (d, 1H, J=8.4 Hz), 6.26 (dd, 1H, J=2.8, 8.8 Hz), 6.00 (d, 1H, J=2.8 Hz), 5.65 (s, 1H), 3.93 (s, 3H), 3.66 (s, 3H), 2.37 (s, 3H).

The synthetic route of 2-Chloro-5-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OssiFi Inc.; Ellies, Debra; Rey, Jean-Philippe; Kimball, F. Scott; US2014/288068; (2014); A1;,
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Related Products of 103724-99-8, A common heterocyclic compound, 103724-99-8, name is 2-Bromo-5-chloro-1,3-dimethylbenzene, molecular formula is C8H8BrCl, 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 400 mL vessel equipped with a mechanical stirrer, thermometer, distillation head and dropping funnel, solid sodium hydroxide (10.9 g, 0.27 mol, microprills with 0.5 – 1 mm diameter) is charged under an inert atmosphere.1-Methyl-2-pyrrolidone (NMP, 137 g) is added to the vessel in one portion through the dropping funnel and the reaction mixture cooled to 10 – 15 C while stirring. A solution of malononitrile (NEC-CH2-CEN) (6.6 g, 0.10 mol) in NMP (8.9 g) is added through the dropping funnel over 10 – 15 minutes maintaining the temperature at 10 – 15 C. The reaction mixture is then heated to 100 C and a vacuum (30 mbar) applied, upon which solvent (40 g) is distilled off.2-Bromo-5-chloro-1 ,3-dimethyl-benzene (20 g, 0.089 mol) is then added through the dropping funnel over 5- 10 minutes, whilst maintaining the temperature at 100- 110 CC. A mixture containingpalladium (II) chloride (0.19 g, solution in conc. hydrochloric acid, assay 20% Pd, 0.36 mmol), triphenylphosphine (0.45 g, 1.6 mmol) and NMP (18 g) is then added through the dropping funnel over a 5 – 10 minute period. The temperature is allowed to rise to 124 C and the reaction mixture stirred at this temperature for 2 – 3 hours. Conversion is monitored by pulling samples and subsequent HPLC analysis.When conversion is complete, a vacuum (20-40 mbar) is applied and solvent (90 g) is distilled off. The resulting residue is cooled below 100 C and water (95 g) is added. After cooling to room temperature, the resulting mixture is filtered through hyflo (Hyflo SuperCel diatomaceous earth, ca. 10 g) and the filter cake washed with water (20 g). To the combined filtrates, hydrochloric acid (20.6 g, assay 32%, 0.18 mol) is added to adjust the pH from 13.3 to 2.7.The resulting mixture is extracted with tert-butyl-methyl ether (2 x 110 g). The organic phases are washed with water (2 x 50g) and the combined organic phases evaporated to dryness. The resulting solid residue is recrystallized from iso-propanol (63 g) and the resulting crystals filtered, washed with cold iso-propanol (5 g) and dried under vacuum to yield 2-(4-chloro-2,6-dimethyl-phenyl)propanedinitrile (melting point (m.p.) 145 – 147 C).

The synthetic route of 103724-99-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; ZELLER, Martin; FEDOU, Nicolas; (19 pag.)WO2018/15489; (2018); A1;,
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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. 4863-91-6, name is 3-Chloro-5-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

A mixture of Example A47 (200 mg, 0.363 mmol), DIEA (188 mg, 1.452 mmol) and 3-chloro-5-fluoroaniline (211 mg, 1.452 mmol) in dioxane (5 mL) was heated at 80 C. overnight. The mixture was cooled to RT, treated with EtOAc and satd. NaHCO3 and the resulting solid collected via filtration and dried to afford crude 1-(4-chloro-5-(1-ethyl-7-((4-methoxybenzyl)(methyl)amino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(3-chloro-5-fluorophenyl)urea (91 mg, 39% yield) which was carried on to the next step without further purification. MS (ESI) m/z: 638.2 [M+H]+.

According to the analysis of related databases, 4863-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Petillo, Peter A.; US8461179; (2013); B1;,
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Some common heterocyclic compound, 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, molecular formula is C6H2ClF3O2S, 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. Recommanded Product: 220227-21-4

A solution of ferf-butyl thiazol-4-ylcarbamate (3.46 g, 17.3 mmol) in tetrahydrofuran (150 mL) at -78 C was treated with lithium 6/’s(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran, 20.8 mL, 20.8 mmol). The resulting mixture was stirred at -78 C for 0.5 h, allowed to warm to ambient temperature and stirred for a further 0.5 h. The reaction mixture was cooled to -78 C and treated with a solution of 2,4,5- trifluorobenzene-1-sulfonyl chloride (3.99 g, 17.3 mmol) in tetrahydrofuran (30 mL). The resulting mixture was stirred at -78 C for 4 h, allowed to warm to ambient temperature and stirred for a further 16 h. The reaction mixture was diluted with ethyl acetate (300 mL) and washed with saturated aqueous ammonium chloride (2 x 150 mL) and brine (2 x 150 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a gradient of ethyl acetate in hexanes to afford terf-butyl thiazol-4-yl((2,4,5- trifluorophenyl)sulfonyl)carbamate as a beige solid in 62% yield (4.23 g): 1H NMR (300 MHz, CDCI3) 6 8.79-8.75 (m, 1 H), 8.06-7.96 (m, 1 H), 7.53-7.48 (m, 1H), 7.15-7.04 (m, 1 H), 1.34 (s, 9H); MS (ES+) m/z 394.7 (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 220227-21-4, its application will become more common.

Reference:
Patent; XENON PHARMACEUTICALS INC.; LIU, Shifeng; FOCKEN, Thilo; CHAHAL, Navjot; ZHANG, Zaihui; OBALLA, Renata, Marcella; FONAREV, Julia; WO2013/64984; (2013); A1;,
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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. 146447-18-9, name is 5-Bromo-2-chloro-4-fluoroanisole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H5BrClFO

1.0 g (4.2 mmol) of 5-Bromo-2-chloro-4-fluoroanisole, 47 mg (0.21 mmol) of palladium acetate, 180 mg (0.29 mmol) of binap, 0.65 g (6.7 mmol) of sodium tert-butoxide, and 3.6 g (42 mmol) of piperazine in 3 mL of dry toluene werw heated at 110 C. for 24 hours. The reaction was partitioned between ethyl acetate and water, and the phases were separated. The ethyl acetate phase was washed once each with water and brine, and was concnentrated. The residue was purified by chromatography to give 1-(4-Chloro-2-fluoro-5-methoxy-phenyl)-piperazine.

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 146447-18-9.

Reference:
Patent; ChemoCentryx, Inc.; US2004/162282; (2004); A1;,
Chloride – Wikipedia,
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Application of 14752-66-0,Some common heterocyclic compound, 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, molecular formula is C6H4ClNaO2S, 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: A mixture of the sodium arylsulfinate (1 mmol), Cu(OAc)2 (0.5 mmol)and CH3CN (1 mL) was stirred at 60 C in air for 3 h. After this, themixture was cooled to room temperature and filtered through a filterpaper. The organic phases were evaporated under reduced pressure andthe residue was subjected to flash column chromatography (silica gel,ethyl acetate/petroleum ether = 1/10) to obtain the desired product.All products are known compounds and were characterised by 1HNMR, 13C NMR and HRMS.

The synthetic route of 14752-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Peng, Yao; Journal of Chemical Research; vol. 38; 5; (2014); p. 265 – 268;,
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Synthetic Route of 53531-69-4, 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. 53531-69-4, name is (4-Bromophenyl)methanesulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Various alkyl halides 23a-k (2.5 mmol) and thiourea (0.19 g, 2.5 mmol) were refluxed together in EtOH (2.5 mL) for 1 h. Afterr emoval of EtOH at reduced pressure, the obtained solid was slowly added to a mixture of NCS (1.33 g, 10 mmol), 2 M HCl (0.68 mL) and MeCN (4 mL) over 15 min. Upon completion of the reaction (TLC monitoring), the solvent was removed under vacuum. Then H2O(5 mL)was added to the residue and stirred for 15 min, the resulting solid was filtered and dried under an infrared lamp to afford the corresponding sulfonyl chlorides 24a-k. Without further purification, 24a-k was added in portions to a solution of NaN3 (195 mg ,3 mmol) in acetone/H2O (10 mL, acetone/H2O = 1:1) at 0 C. After being stirred at room temperature for 4 h, the reaction mixtur ewas concentrated in vacuo and H2O (10 mL) was added to the residue. The aqueous solution was extracted with CHCl3 (3 x 10 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford sulfonyl azides 25a-k.

The synthetic route of (4-Bromophenyl)methanesulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fang, Sen-Biao; Li, Hui-Jing; Nan, Xiang; Wu, Rui; Wu, Yan-Chao; Zhang, Jing; Zhang, Zhi-Zhou; European Journal of Medicinal Chemistry; vol. 200; (2020);,
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Synthetic Route of 2687-12-9, These common heterocyclic compound, 2687-12-9, name is Cinnamyl 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 flame dried 100 mL round-bottomed flask under Ar was charged with chlorotrioctylstannane (2.0 g mL, 4.05 mmol), cinnamyl chloride (0.8 g, 5.3 mmol),magnesium powder (0.14 g, 5.7 mmol), a crystal of iodine and dry THF (50 mL). The resulting mixture was sonicated at 50 C for 6 h and was then stirred overnight at room temperature. Water (50 mL) was added and the mixture was transferred to a separating funnel. The water layer was separated and the remaining organic layer was diluted with heptane (100 mL), washed with acetonitrile (2 x 50 mL), water (50 mL) and finally againwith acetonitrile (3 x 50 mL). Drying on MgSO4, filtration and concentration in vacuo afforded a crude product, which was purified by column chromatography on silica gel using petroleum ether as the eluent, providing trioctyl(3-phenylallyl)stannane (1.42 g, 2.5 mmol, 62 %) as a faint yellow oil. ?H-NMR (CDC13, 400 MHz) & 7.40-7.26 (m, 2H), 7.25-7.20 (m, 2H), 7.12-7.06 (m, 1H),6.39 (dt, 1H, I = 15.5, 8.8 Hz), 6.17 (dt, 1H, I = 15.5, 1.0 Hz), 2.04-1.84 (m, 2H), 1.68-1.40 (m, 6H), 1.36-1.16 (m, 30H), 0.98-0.82 (m, 15 H); ?3C-NMR (100 MHz, CDC13):138.9, 131.3, 128.5, 125.8, 125.3, 125.1, 34.5, 32.0, 29.4, 29.3, 27.0, 22.8, 16.3, 14.2, 10.0;?9Sn-NMR (149.2 MHz, CDC13) & -12.8.

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

Reference:
Patent; UNIVERSITEIT ANTWERPEN; KUVSHINOV, Alexandr; FRANCK, Philippe; DEPRAETERE, Stefaan; MAES, Bert; DE HOUWER, Johan; WYBON, Clarence; STERCKX, Hans; SERGUEEV, Serguei; WO2013/167585; (2013); A2;,
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These common heterocyclic compound, 108-41-8, name is 1-Chloro-3-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. SDS of cas: 108-41-8

General procedure: Under N2 atmosphere, KOtBu (1.0 mmol), NHC-Pd(II)-Im 2a (1.0 mol %), dry dioxane (1.0 mL), morpholine 3 (0.8 mmol), and aryl chloride 4 (0.7 mmol) were successively added into a Schlenk reaction tube. The mixture was stirred at 70 C for 3 h. The solvent was removed under reduced pressure and the residue was purified by a flash chromatograph on silica gel to give the pure products 5.

The synthetic route of 1-Chloro-3-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhu, Lei; Gao, Ting-Ting; Shao, Li-Xiong; Tetrahedron; vol. 67; 29; (2011); p. 5150 – 5155;,
Chloride – Wikipedia,
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