Month: June 2021

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. 106-39-8, name is 1-Bromo-4-chlorobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-4-chlorobenzene

General procedure: A mixture of aryl halide (1 mmol), alkene (1.2 mmol), K2CO3(2 mmol) and MNPs-Mel-Pd (0.02 g) was stirred in DMF at 100 Cand the progress of the reaction was monitored by TLC. Aftercompletion of the reaction, the catalyst was separated using anexternal magnet, the mixture was cooled to room temperature andthe product was solidified by addition of water to the mixture andpure products were obtained in yields of 76-99%. The chromatographictechniques were not used to isolate the products.

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:
Article; Bodaghifard, Mohammad Ali; Journal of Organometallic Chemistry; vol. 886; (2019); p. 57 – 64;,
Chloride – Wikipedia,
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Application of 72235-58-6, 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 72235-58-6 as follows.

Example 7; 3- [5,6-Bis(methyloxy)-2-pyridinyll -N- [(4-chloro-3-fluorophenvDmethyll -2,4-dioxo-l ,2,3,4- tetrahvdrothieno[3,2-Patent; GLAXOSMITHKLINE LLC; SCHULZ, Mark, James; WANG, Younghui; GHERGUROVICH, Jonathan M.; WO2010/59555; (2010); A1;,
Chloride – Wikipedia,
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Related Products of 63624-28-2, 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. 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

B) 5-Chloro-3-(2-ethoxyphenyl)-1-[(2,4-dimethoxyphenyl)sulphonyl]-3-[2-oxo-2-[4-(4-pyridyl)-1-piperazinyl]ethyl]-1,3-dihydro-2H-indol-2-one 0.085 g of 60% sodium hydride in oil is added to a mixture of 0.9 g of the compound obtained in the preceding step in 20 ml of a THF/DMF mixture (90/10; v/v), and the mixture is stirred at RT for 15 minutes. 0.45 g of 2,4-dimethoxybenzenesulphonyl chloride is then added and the mixture is stirred at RT for 30 minutes.The reaction mixture is poured into water and extracted with EtOAc, the organic phase is washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum.The residue is chromatographed on silica gel, eluding with a DCM/MeOH mixture (96/4; v/v).0.42 g of the expected product is obtained after crystallization from iso ether, m.p.=225 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

Some common heterocyclic compound, 10061-02-6, name is trans-1,3-Dichloropropene, molecular formula is C3H4Cl2, 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. Safety of trans-1,3-Dichloropropene

To a solution of i-Pr2NH (7.06 mL, 50.4 mmol, dried over CaH2) in dry THF (50 mL) cooled at -78 C under N2 was added n-BuLi (24.6 mL, 49.2 mmol, 2.0 M) dropwise. The resultant solution was allowed to warm to 0 C followed by stirring for 1 h at the same temperature to form a yellow solution of lithium diisopropylamide (LDA).To the above prepared LDA solution cooled at -78 C, was added slowly methyl acetoacetate (2.59 mL, 24 mmol) followed by stirring at 0 C for 1 h. To the resultant solution cooled at -78 C was added a solution of (E)-1,3-dichloropropene (1.85 mL, 20 mmol) in dry THF (10 mL) using a syringe followed by stirring for 10 min at the same temperature. The reaction was allowed to warm to 0 C; after stirringat 0 C for 16 h and at room temperature for another 2 h, the reaction was quenched by addition of H2O (50 mL). The reaction mixture was extracted with EtOAc (50 mL x 3). The combined organic layer was washed with brine (50 mL) and dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel (17% EtOAc in hexane) to afford the product 44 (3.31 g, 87%) as a colorless oil. IR (film): 2955, 2929, 1747, 1717, 1633,1438, 1323, 1261 cm1; 1H NMR (400 MHz, CDCl3) d 5.96 (d,J 13.2 Hz, 1H), 5.82 (dt, J 13.2, 7.2 Hz, 1H), 3.68 (s, 3H), 3.41 (s,2H), 2.61 (t, J 7.2 Hz, 2H), 2.30 (dt, J 7.2, 7.2 Hz, 2H); 13C NMR(100 MHz, CDCl3) d 201.2, 167.4, 131.7, 118.4, 52.5, 49.0, 41.8, 24.6;HRMS (CI) calcd for C8H12ClO3 191.0475 (MH), found 191.0470 and C8H1237ClO3 193.0445 (MH), found 193.0448.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10061-02-6, its application will become more common.

Reference:
Article; Su, Ye-Xiang; Dai, Wei-Min; Tetrahedron; vol. 74; 13; (2018); p. 1546 – 1554;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 766545-20-4, name is 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine 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. COA of Formula: C8H10Cl2N2

To a slurry of 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride (106.1 g, 517 mmol, commercially available from D-L Chiral Chemicals, ST-0143) and N,N-diisopropylethylamine (80 g, 108 mL, 621 mmol, 1.2 eq) in DCM (1 L) was added a solution of di-tert-butyl dicarbonate (119 g, 543 mmol, 1.05 eq) in DCM (100 mL) via an addition funnel within 1 hr. The reaction mixture became a clean solution and the solution thus obtained was stirred at room temperature for an additional hour and monitored using LCMS. Upon completion, the reaction mixture was concentrated. The residue was dissolved in EtOAc (1 L) and washed with water (3*300 mL), washed with brine (300 mL) and dried over Mg504. The solvent was evaporated under vacuum to give the title compound as an off-white solid (139 g, yield: 100%). 1H NMR (400 MHz, CDCl3) delta ppm 1.49 (9H, s), 2.97 (2H, t, J=5.9 Hz), 3.73 (2H, t, J=6.0 Hz), 4.57 (2H, s), 7.17 (1H, d, J=8.0 Hz), 7.38 (1H, d, J=8.0 Hz) ppm; LCMS m/z: 269 (M+1).

The synthetic route of 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; US2012/244110; (2012); 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. 102-49-8, name is 3,4-Dichlorobenzylamine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 102-49-8

tert-butyl(2-(N-cyclohexylacrylamido)ethyl)(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate (100 mg, 0.205 mmol) and (3,4-dichlorophenyl)methanamine (72 mg, 0.41 mmol) were dissolved in ethanol (1 mL) and heated at 50° C. for 20 hours. The solvent was evaporated in vacuo and the residue dissolved in dichloromethane (1 mL). Trifluoroacetic acid (1 mL, 13 mmol) was added and the mixture stirred for 2 hours, and then concentrated under reduced pressure. The residue was purified by prep-HPLC with (eluting with acetonitrile and 0.2percent aqueous trifluoroacetic acid) to afford the title compound (125 mg, 0.155 mmol, 76percent yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 10.04-9.98 (m, 1H), 9.94-9.84 (m, 1H), 8.81 (s, 2H), 8.43 (s, 1H), 7.88-7.80 (m, 1H), 7.80-7.72 (m, 1H), 7.56-7.46 (m, 1H), 6.70-6.62 (m, 1H), 6.52-6.41 (m, 1H), 4.57-4.48 (m, 2H), 4.27-4.18 (m, 2H), 3.56-3.41 (m, 1H), 3.17-3.03 (m, 5H), 2.98 (d, J=12.0 Hz, 2H), 2.76 (dq, J=14.9, 6.9 Hz, 4H), 1.82-1.74 (m, 2H), 1.71-1.58 (m, 3H), 1.56-1.17 (m, 4H), 1.15-1.03 (m, 1H). MS (ESI+) 563.3 [M+H]+.

According to the analysis of related databases, 102-49-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AbbVie Inc.; Chiang, Gary G.; Pappano, William N.; Sweis, Ramzi F.; Wang, Zhi; (23 pag.)US2016/31838; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 823-57-4,Some common heterocyclic compound, 823-57-4, name is 2-Bromo-5-chloroaniline, molecular formula is C6H5BrClN, 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.

2-Bromo-5-chloroaniline 81a (4.13g, 20.0mmol), was dissolved in 50mL ethyl acetate was added 1- (t-butoxycarbonyl) azetidine-3-carboxylic acid (4.83g, 24.0 mmol), triethylamine (4.05g, 40.00mmol), 0°C dropwise tri-n-propyl phosphoric anhydride (74.35g, 116.84mmol), stirred for 16 hours at room temperature. 50mL of water was added, extracted with ethyl acetate (50mL × 3), the combined organic phase was washed with water (50mL × 2), washed with saturated sodium chloride solution (50mL × 2), dried over anhydrous sodium sulfate, filtered, and the filtrate under reduced pressure and concentrated to give tert-butyl 3 – ((2-bromo-5-chlorophenyl) carbamoyloxy azetidine-1-carboxylate 81b (7.3g, pale yellow solid), yield: 84.3percent.

The synthetic route of 823-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Mingde New Drug Research And Development Co. Ltd; HE, HAI-YING; SHI, WEI-HUA; JIANG, ZHI-GAN; HAN, LI-XIA; SUN, JI-KUI; LI, JIAN; CHEN, SHU-HUI; (175 pag.)TW2016/5834; (2016); A;,
Chloride – Wikipedia,
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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. 108-70-3, name is 1,3,5-Trichlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,3,5-Trichlorobenzene

In a nitrogen-filled glove box, a 50 mL pressure flask wascharged with 1,3,5-trichlorobenzene (13.68 g, 75.40 mmol),0.67 mL of chloroform (1.00 g, 8.37 mmol), aluminum trichloride(1.22 g, 9.14 mmol), and a magnetic stir bar. This mixture washeated to 90 C for 2 h under an atmosphere of nitrogen. After thistime the mixture was allowed to cool to room temperature and 20 ml of HCl (0.1N) was added drop-wise over this mixture whichwas cooled in an ice bath. The purple suspension immediatelyturned into a yellow solution that was then extracted from theaqueous byproducts using 50 mL of chloroform in a separatoryfunnel. The organic layer was dried over magnesium sulfate for 1 hand filtered over a scintillated glass frit. The yellow solution wasimmediately concentrated under vacuum and the obtained oilymaterial was added to 40 mL of hexanes which resulted in theimmediate precipitation of a white solid. The solid was collected ona frit, and washed with hexanes until the washings were colorless.The white solid was dried under vacuum to get an 80% yield whichwas used in the next step without further purification. m.p. 246-248C. 1H NMR (400 MHz) (CDCl3): d 6.68 (s, 1H, CHPh), 7.23e7.24(d, 3H, J 2.3 Hz), 7.35e7.36 (d, 3H, J 2.3 Hz). 13C NMR(100.61 MHz): delta 49.80(CH), 128.43, 130.00, 133.78,133.82, 137.07,137.90. The synthesis has been modified slightly and the purificationprocess as well. Characterization data of this compound is inagreement with those reported in the literature [16].

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 108-70-3.

Reference:
Article; Neier, Eric; Arias Ugarte, Renzo; Rady, Nader; Venkatesan, Swaminathan; Hudnall, Todd W.; Zakhidov, Alexander; Organic electronics; vol. 44; (2017); p. 126 – 131;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2267-25-6, name is 2-Chloro-4-fluoroanisole, molecular formula is C7H6ClFO, 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-Chloro-4-fluoroanisole

Sodium hydride (60% dispersion in mineral oil, 31 mg, 0.776mmol) was added to an ice- cooled solution of the product of preparation 20 (135mg, 0.388mmol) in N1N- dimethylformamide (4mL) and the mixture was stirred at O0C for 15 minutes. 2-chloro-4-fluoro- anisole (93mg, 0.582mmol) in N,N-dimethylformamide (1mL) was added and the mixture was stirred for 16 hours, at 5O0C. The solution was cooled to 250C and sodium hydride (60% dispersion in mineral oil, 62mg, 1.55mmol) was added and the solution was stirred for 16 hours at 80C. The reaction mixture was then cooled to 25C and quenched with water (3mL), concentrated in vacuo and the aqueous residue was partitioned between ethyl acetate (2OmL) and water (5mL). The aqueous layer was separated and extracted with ethyl acetate (2x20mL). The combined organic solution was washed with brine (1OmL), concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with pentane: (ethyl acetate:methanol;0.88ammonia, 90:10:1), 3:1 to 1:1. The product containing fractions were evaporated under reduced pressure and the residue was further purified using an Isolute SCX-2 cartridge, eluting with methanol followed by 1M ammonia in methanol. The basic fractions were evaporated to afford the title compound as a yellow gum in 32% yield, 61mg.1HNMR(400MHz, CD3OD) delta: 1.03(s, 3H), 1.08(s, 3H), 1.28-1.31(m, 2H), 1.76-1.80(m, 1H), 1.86-1.93(m, 1H), 2.09-2.18(m, 1H), 2.49-2.63(m, 2H), 2.67-2.70(m, 1 H), 2.76-2.87(m, 2H), 3.80(s, 3H), 4.71-4.75(m, 1H), 6.74-6.77(dd, 1H), 6.89-6.95(dd, 1H), 7.24-7.46(m, 10H), 8.45- 8.59(m, 1 H); LRMS APCI m/z 489 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2267-25-6, its application will become more common.

Reference:
Patent; PFIZER LIMITED; WO2007/34325; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2533-69-9, 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. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 2,2,2-trichloroacetimidate (1.53 g) in acetic acid (10 ml) was added a solution of 4-fluorobenzene-1,2-diamine in acetic acid (10 ml) under ice-cooling, followed by stirring at room temperature for 3 hours. The reaction liquid was concentrated under reduced pressure and to the obtained residue was added water, followed by neutralization with a saturated aqueous sodium hydrogen carbonate solution and extraction with EtOAc. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from iPr2O/EtOAc/MeOH to obtain 5-fluoro-2-(trichloromethyl)-benzimidazole (1.5 g) as a beige powder.

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

Reference:
Patent; Astellas Pharma Inc.; EP2351749; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics