Category: chlorides-buliding-blocks

Reference of 33406-96-1, A common heterocyclic compound, 33406-96-1, name is 1-Chloro-4-fluoro-2-methylbenzene, molecular formula is C7H6ClF, 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: A mixture of aryl chloride (0.125 mmol), aryl boronic acid (0.15 mmol) and K4PO3 (0.25 mmol), catalyst (0.000125 mmol) in H2O (0.1 mL), isopropanol (0.1 mL) was stirred in a test tube at 45 C. After the reaction was completed, cooled to room temperature and the mixture was extracted with CH2Cl2 and dried over Na2SO4. The solvent was removed under vacuum. The product was purified by flash chromatography on a silica gel column. The characterization of all coupling products see Supporting Information.

The synthetic route of 33406-96-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Fangwai; Li, Yanji; Liu, Guiyan; Lu, Qingwen; Ni, Chang; Zeng, Yongfei; Zhang, Rong; Zhang, Xue; Zhang, Yingying; Zhao, Yuxuan; Tetrahedron Letters; (2019);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 18282-59-2 as follows. Quality Control of 4-Bromo-1,2-dichlorobenzene

A. 1-Bromo-4,5-dichloro-2-nitro-benzene. 4-Bromo-1,2-dichlorobenzene (10.5 g, 46.3 mmol) was added to 25 mL concentrated sulfuric acid at 0° C. A 1:1 mixture of 70percent nitric acid and concentrated sulfuric acid (20 mL) was added dropwise over 40 min. The reaction mixture was allowed to warm to ambient temperature with stirring over 0.5 h, then was poured onto cracked ice. The resulting mixture was filtered through paper, and the collected solids were washed with water (5*) and then dried at 45° C. under reduced pressure for 30 min to provide 10.7 g of an 88:12 mixture of desired nitroarene to starting material. Recrystalization from absolute ethanol provided 4.76 g of long yellow needles corresponding to a 20:1 mixture of product to starting material. The mother liquor was concentrated and recrystallized twice to provide an additional 1.18 g of product (17:1 mixture with recovered starting material). TLC (silica gel, 1:1 hexanes/EtOAc): Rf=0.45. 1H NMR (400 MHz, CDCl3): 7.95 (s, 1H), 7.80 (s, 1H).

According to the analysis of related databases, 18282-59-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allison, Brett; McAtee, Laura C.; Phuong, Victor K.; Rabinowitz, Michael H.; Shankley, Nigel P.; US2004/224983; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, 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 918538-05-3, name: 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

General procedure: To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, and friends who are interested can also refer to it.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 63624-28-2, name is 2,4-Dimethoxybenzene-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. Application In Synthesis of 2,4-Dimethoxybenzene-1-sulfonyl chloride

B) 3-(2-Chlorophenyl)-1-[(2,4-dimethoxyphenyl)sulphonyl]-5-methyl-3-[2-oxo-2-[4-(2-pyridyl)-1-piperazinyl]ethyl]-1,3-dihydro-2H-indol-2-one 0.0335 g of 60% sodium hydride in oil is added, at RT, to a mixture of 0.3 g of the compound obtained in the preceding step in 10 ml of THF, and the mixture is stirred for 30 minutes. 0.2 g of 2,4-dimethoxybenzenesulphonyl chloride is then added and the mixture is stirred at RT for 1 hour. 50 ml of water are added to the reaction mixture and the resulting mixture is extracted with EtOAc, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum.The residue is chromatographed on silica gel, eluding with a DCM/MeOH mixture (98/2; v/v).0.32 g of the expected product is obtained after crystallization from iso ether, m.p.=239 C.

The synthetic route of 2,4-Dimethoxybenzene-1-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Di Malta, Alain; Garcia, Georges; Roux, Richard; Schoentjes, Bruno; Serradeil-Le Gal, Claudine; Tonnerre, Bernard; Wagnon, Jean; US2004/180878; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 22680-44-0, These common heterocyclic compound, 22680-44-0, name is (2-Chlorophenyl)methanamine 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.

(ii) 1-(2-chlorophenyl)methyl-2-propyl-2-thiopseudourea A solution of 2-chlorobenzylamine hydrochloride (41 g, 0.23 mol) and ammonium thiocyanate (19.28 g, 0.253 mol) in water (170 mL) was heated on the steam bath for 18 hours. This mixture was concentrated in vacuo, and the residue was taken up in toluene (1 L) and azeotroped with a Dean-Stark head. The residue was triturated with wet diethyl ether to provide 27.6 g (60%) of 1-(2-chlorophenyl)methyl thiourea. The product was recrystallized from ethanol; mp 120-122 C. A mixture of 1-(2-chlorophenyl)methyl thiourea (3 g, 14.9 mmol) and propylbromide (13.5 g, 110 mmol) in acetonitrile (20 mL) was refluxed for 5 hours. The solvent was evaporated, the residue was dissolved in 200 mL of 50% water/ether and acidified with 48% hydrobromic acid solution. The two phases were separated, the aqueous layer was washed with ether and then the aqueous layer was basified with 10% sodium carbonate solution. The liberated product was extracted with diethyl ether, washed with water and brine, dried and concentrated to give 1-(2-chlorophenyl)methyl-2-propyl-2-thiopseudourea (2.82 g, 78%); mp 112-114 C.

The synthetic route of 22680-44-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; US5444080; (1995); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 1871-57-4,Some common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, molecular formula is C4H6Cl2, 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 suspension of sodium hydride (purity >55%, 11.4 g)in N,N-dimethylformamide (150 mL), 3-chloro-2-chloromethyl-1-propene (12.7 mL)was added under ice-cooling, and the mixture was stirred at the same temperature for 10 minutes. Then, a solution of 2-(tert-butoxycarbonylamino)-1-ethanol (19.3 g)in tetrahydrofuran (150 mL)was added dropwise over 1.5 hours, and the mixture was stirred at room temperature for 2.5 hours. The reaction solution was cooled with ice, then water was added, and then the mixture was extracted with diethyl ether three times. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The resultant was filtered, and concentrated under reduced pressure, then the residue obtained was purified by silica gel column chromatography (hexane/ethyl acetate)to obtain the title compound (16.0 g)as an oil. 1H-NMR (CDCl3)delta: 5.06-4.95 (2H, m), 4.19-4.06 (4H, m), 3.76-3.69 (2H, m), 3.54-3.48 (2H, m), 1.46 (9H, s). MS (m/z): 114 (M-CO2tBu+H)+.

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-2-chloromethyl-1-propene, its application will become more common.

Reference:
Patent; Daiichi Sankyo Co., Ltd.; NAITO, Hiroyuki; KAGOSHIMA, Yoshiko; FUNAMI, Hideaki; NAKAMURA, Akifumi; ASANO, Masayoshi; HARUTA, Makoto; SUZUKI, Takashi; WATANABE, Jun; KANADA, Ryutaro; HIGUCHI, Saito; ITO, Kentaro; EGAMI, Akiko; KOBAYASHI, Katsuhiro; EP3643703; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene, molecular formula is C6H3Cl2F, 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. Product Details of 1435-48-9

In a 10001111 four-necked flask, 2,4-dichlorofluorobenzene was charged15 (^ (0.911111), cooling to 20 (: adding aluminum chloride 200. 2g (l.5mol), in the 20 ~ 30 CAdd acetyl chloride 78. 5g (l. Omol), 2 ~ 3h plus finished.Slowly heat up to 40 C and incubate for 30 min, then slowly heat up to 70 C and incubate for 1 ~ 2h, then slowly heat up to 110 C, 110 ± 2 CHeat 3 ~ 4h, cooling, add 500g 5% hydrochloric acid, hydrolysis at 80 ~ 90 C 2 ~ 3h, after washing to neutral, there areThe phase of the product was recrystallized from the second distillation to obtain 168 g of 2,4-dichloro-5-fluoroacetophenone in an amount of 99.8%. The yield was 89.3%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1435-48-9, its application will become more common.

Reference:
Patent; Binhai Yongtai Medical Chemical Co Ltd; He, Renbao; Shao, Hongming; (8 pag.)CN102249881; (2016); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, 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 61881-19-4, SDS of cas: 61881-19-4

Disaccharide 92 (1.0 g, 1.03 mmol) was dissolved in a mixture of CH3CN/ /H20 (30 mL/7.5 mL). Ceric ammonium nitrate (1.69 g, 3.09 mmol) was added to the solution at 0 C and then the mixture was stirred at room temperature under N2 for 2 h. The mixture was concentrated to dryness and the residue was diluted with DCM (100 mL) and the organic phase was washed with H20 and then dried over Na2S04, filtered and the solvents were removed in vacuum. Silica gel column chromatography (3:2 hexanes-EtOAc) afforded the corresponding hemiacetal 93 (730 mg, 82%>). Compound 93, N-phenyltrifluoroacetimidoyl chloride (0.68 mL, 4.2 mmol) and DCM (50 mL) was cooled down to 0 C. DBU (127 mu, 0.95 mmol) was added and the mixture was stirred at room temperature for 1 h. The mixture was concentrated. Silica gel column chromatography (2: 1 hexanes-EtOAc) afforded the disaccharide donor 3 as a white solid (650 mg, 75%>).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.; BOONS, Geert-Jan; WANG, Zhen; WO2012/135049; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 501-29-1, These common heterocyclic compound, 501-29-1, name is 1-Chloro-2-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.

Tetrahydrofuran (8.35 L) into a 3-L four-neck flask equipped with a mechanical stirrer, an addition funnel and a temperature probe under N2 atmosphere. Charged 4-Chloro-3-fluoroanisole (1000 g) to a 3-L four-neck flask equipped with a mechanical stirrer, an addition funnel and a temperature probe. Cooled the reaction mass to -60 C. to -70 C. Added n-Butyl Lithium in hexanes (30%, 1.42 kg) in to reaction mass through canula under nitrogen atmosphere slowly, while maintaining the temperature of the reaction mass below -60 C. Maintained the reaction at below -60 C. for 2 h. Meanwhile Iodine solution prepared by dissolving Iodine (2.405 kg) in Tetrahydrofuran (2.4 L) at 25-28 C. Transferred the Iodine solution in step 6 into a clean addition funnel with THF (500 mL) rinse. Added Iodine solution from the addition funnel to the reaction over 120 min while maintaining the internal temperature at <-60 C. Removed cooling bath and allowed to attain -5 C. to 0 C. Submitted the IPC sample when it reaches -5 C. to 0 C.1. A sample was removed at -2 h and checked by HPLC-97.06 AP; Int-01-0.59 AP. Work Up: Quenched the reaction with 20% Na2SO2O3 solution (1.015 kg of sodium thiosulphate dissolved in 5.1 L of DM water) while maintaining the internal temperature at <10 C. Allowed RM to warm to RT. Transfer resulting biphasic mixture into separating funnel, rinse the flask with THF (1.2 L; 1.0-1.5 Vol wrt Int-1), and transfer to separating flask. Removed and retain bottom aqueous phase for further extraction. Concentrated the organic layer. Dissolved concentrated mass in EtOAc (8.0 L; 8.0-8.5 Vol wrt Int-1) Extract the retained aqueous phase with EtOAc (7.1 L: 7.0-7.5 Vol wrt Int-1). Combined all organic phases, Rinse the flask with EtOAc (1.0 L; 1.0-1.5 Vol wrt Int-1). Washed organic phases with DM water (5.7 L; 5.0-6.0 Vol wrt Int-1). Concentrated the organic layer2 on rotovap at 45-50 C. completely. Purification: Added Acetonitrile (5.1 L; 5.0-5.5 vol wrt Int-01). Warmed to 55 C. to dissolve all solid. Rotate the above mass in rotavapor flask at 55 C. for 10 min. Cooled to ambient temperature. Transferred the mass into a clean reactor, rinse the flask with Acetonitrile (1.0 L; 1.0-1.2 vol wrt Int 01) and add rinse into reactor. Added water (1 L; 1.0-1.2 vol wrt Int-01) in to reactor with stirring. Stirred the resulting slurry for 15 min. Added water (5.3 L; 5.0-5.5 Vol wrt Int-01) over 15 min. Stirred the above mass at ambient temperature for 15 min. Unload the mass into a container, rinsed the reactor with water (1 L; 1.0-1.2 vol wrt Int-01), and collected the rinse in same container. Filtered the solid. Rinsed the container with water (1 L; 1.0-1.2 vol wrt Int-01), filtered the rinse. Washed filter cake with water (3.3 L; 3.0-3.5 Vol wrt Int-01). Suck dried for 2 h, then dried at 55 C. in VTD for 15 h. Unload the material. (LOD should be less than 1%). Wt: 1533 g (85.9% yield). Description (color and appearance): Off White crystalline solid. HPLC RT Time 4.897 min Under following conditions: Detector: 210 nm; Injection volume 5.00 muL; Run Time 15 min; Column. YMC UltraHT Pro C18 (50 mm×3.0 mm), 2.0mu; Mobile Phase A-0.05% TFA in MillQ Water; Mobile Phase B-0.05% TFA in Acetonitrile; Flow: 1.0 mL/min; Column Oven-40 C.; Time (min)-0 05 10 12 15; B Conc.-10 90 90 10 10. NMR: (1H NMR, 400 MHz, dmso-d6) delta 7.58 (t, 8.8 Hz, 1H), 6.89 (m, 1H), 3.87 (s, 3H). The synthetic route of 501-29-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Bristol-Myers Squibb Company; Yeung, Kap-Sun; Kadow, John F.; US2013/203775; (2013); A1;,
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. 14862-52-3, name is 3,5-Dibromochlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: chlorides-buliding-blocks

General procedure: A mixture of 1,3-dibromo-5-chlorobenzene (2 g, 7.41 mmol), 9Hcarbazole(2.60 g, 15.56 mmol), tris(dibenzylideneacetone)dipalladium(339 mg, 0.37 mmol), 2-dicyclohexylphosphino-2?,6?-dimethoxy-1,1?-biphenyl (457 mg, 1.11 mmol) and sodium tert-butoxide (2.85 g,29.64 mmol) in 100 ml of toluene were heated at 80 C for 4 h underargon. After cooling down to room temperature, the mixture was extractedwith dichloromethane. The combined organic extracts weredried over Na2SO4 and evaporated under reduced pressure. The crudeproduct was purified by column chromatography on silica gel usingpetroleum ether/dichloromethane (PE/DCM, 8/1, v/v) as the eluent toafford the target compound (2.46 g, 75%).

The synthetic route of 14862-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ran, Quan; Zhang, Yuan-Lan; Hua, Xiaochen; Fung, Man-Keung; Liao, Liang-Sheng; Fan, Jian; Dyes and Pigments; vol. 162; (2019); p. 632 – 639;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics