Author: Jessica.F

Reference of 56961-77-4, A common heterocyclic compound, 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene, molecular formula is C6H3BrCl2, 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.

Intermediate 1-1 was synthesized according to the following reaction formula. To a 2 L flask was added 1-bromo-2,3-dichlorobenzene (55.0 g, 0.243 mol) and sodium tert-butoxide (72.5 g, 0.755 mol) with 700 mL of toluene and the mixture was refluxed for one hour and stirred. After cooling to room temperature, aniline (45.1 g, 0.485 mol) was added and the temperature was raised. After adding 2,2′-bis (diphenylphosphino) -1,1′-binaphthalene (rac-BINAP) (6.06 g, 9.74 mmole), tris (dibenzylideneacetone) dipalladium (0) (4.46 g, 0.284 mol) dissolved in 30 mL of toluene was slowly added dropwise. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with ethyl acetate and water, and the obtained organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated to obtain the desired product. Intermediate 1-1 (36.0 g, yield 50%) was obtained by column chromatography using ethyl acetate and hexane.

The synthetic route of 56961-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; Gu Gi-dong; Lee Gi-gon; Kim Gong-gyeom; Kim Hyeong-seok; Hwang Seong-seok; Lee Sang-u; (28 pag.)KR2019/37174; (2019); A;,
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Electric Literature of 363-51-9,Some common heterocyclic compound, 363-51-9, name is 2-Chloro-6-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.

Example 39: 1 -( r2-(Butyloxy)phenvnmethyl)-Lambda/-(2-chloro-6-fluorophenyl)-1 H- pyrazole-3-carboxamide.; To 1-{[2-(butyloxy)phenyl]methyl}-1 H-pyrazole-3-carboxylic acid (0.558 g, 2.03 mmol) was added thionyl chloride (5 ml, 68.5 mmol) followed by Lambda/,Lambda/-dimethylformamide (0.01 ml, 0.129 mmol). The reaction was stirred at ambient temperature under nitrogen for 22 h. The reaction mixture was concentrated in vacuo, then redissolved in DCM and re-concentrated (x 2) to give 1-{[2-(butyloxy)phenyl]methyl}-1 H-pyrazole- 3-carbonyl chloride as a very pale orange gum which solidified on standing (61 1 mg). To a solution of 2-chloro-6-fluoroaniline (29.1 mg, 0.2 mmol, Avacardo research Chemicals) in chloroform (0.2 ml) was added Lambda/,Lambda/-diisopropylethylamine (0.034 ml, 0.2 mmol) and dimethylaminopyridine (2 mg, 0.016 mmol). 1-{[2- (butyloxy)phenyl]methyl}-1 H-pyrazole-3-carbonyl chloride (29.2 mg, 0.1 mmol) in chloroform (0.2 ml) was then added and the resulting solution stirred and heated at 70 0C under reflux for 2 h. The solvent was removed under a stream of nitrogen and then dimethylsulphoxide (0.6 ml) added. The reaction mixture was purified by MDAP on SUNFIRE C18 column (Method D). The appropriate fraction was concentrated in vacuo then under nitrogen flow to give the title compound (9.8mg); LCMS: (System3) MH+= 402, tRET = 1.33 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-6-fluoroaniline, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; COE, Diane, Mary; COOPER, Anthony, William, James; GORE, Paul, Martin; HOUSE, David; SENGER, Stefan; VILE, Sadie; WO2010/122088; (2010); A1;,
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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. 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Chloro-N,N-dimethylethanamine hydrochloride

General procedure: Requisite alkylaminoethyl chloride hydrochloride, chlorobromopropane and cyclopentyl bromide (6.0mmol) were added to a stirred and refluxing slurry of 4-hydroxybenzaldehyde (1.0g, 8.19mmol) in ethyl methyl ketone (C4H8O) (40ml) in the presence of anhydrous potassium carbonate (2.0g, 14.47mmol). The reaction mixture was further refluxed for 6h with continuous stirring. The completion of the reaction was monitored by TLC. On completion, the reaction mixture was cooled, filtered and the solvent was removed under reduced pressure to obtain an oily residue of corresponding aldehyde 3-9, which was used as such for further reaction.

The synthetic route of 4584-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yadav, Rakesh; Bansal, Ranju; Kachler, Sonja; Klotz; European Journal of Medicinal Chemistry; vol. 75; (2014); p. 327 – 335;,
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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. 98446-49-2, name is 2,4-Dichloro-5-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 98446-49-2

EXAMPLE 18 N-[3-Cyano-4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-quinolinyl]acetamide An amount of 9.7 g (0.035 mol) of N-(4-chloro-3-cyano-6-methoxy-7-quinolinyl)acetamide was stirred in 97 ml of 2-ethoxyethanol. To this were added 2,4-dichloro-5-methoxyaniline (7.4 g, 0.038 mol), and 4.1 g (0.035 mol) pyridine hydrochloride, and the mixture was heated at 135 C. for 3 hours. The solvent was evaporated and the solid was stirred in saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic phase was washed with saturated brine solution, dried over sodium sulfate and evaporated to dryness to give a brown solid (10.7 g, 71% yield), mp 267-270 C.; 1H NMR (DMSO-d6) delta 9.94 (s, 1H), 9.01 (s, 1H), 8.99 (s, 1H), 8.42 (s, 1H), 7.97 (m, 1H), 7.86 (s, 1H), 7.53 (m, 1H), 4.12 (s, 3H), 3.88 (s, 3H), 2.27 (s, 3H); MS (ES) m/z 431.1 (M+1).

According to the analysis of related databases, 98446-49-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Home Products Corporation; US2003/65180; (2003); 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. 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Bromo-3,5-dichlorobenzene

A 250 ml round-bottom flask was charged with magnesium (turnings; 2.68 g; 110 mmol), and argonated. Then, Et2O(60 ml), I2 (one crystal) were added, and a solution of 1-bromo-3,5-dichlorobenzene (25.32 g; 112.1 mmol) in Et2O (80 ml) was added portionwise over 45 min with stirring. After 2 h the mixture was cooled with ice-water bath and AsCl3 (2.8 ml; 33.4mmol) was added dropwise, that caused formation of crystalline precipitate. Stirring was continued at RT for 16 h, and aqueous NH4Cl (100 ml; 10percent) was added. The resulted mixture was extracted with ethyl acetate (3 100 ml), and combined organic phases were washed with brine (100 ml), and dried over MgSO4. The mixture was filtered, evaporated, and residue viscous orange oil was crystallized from n-hexane (dissolved in boiling solvent and slowly cooled to ca. 0 ¡ãC) in three crops(first crop 30 ml; second crop 11 ml; third crop 4 ml) to obtain 8c (14.01 g; 27.31 mmol; 82percent) as a white solid.

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 19752-55-7.

Reference:
Article; Grudzie?, Krzysztof; Basak, Tymoteusz; Barbasiewicz, Micha?; Wojciechowski, Tomasz M.; Fedory?ski, Micha?; Journal of Fluorine Chemistry; vol. 197; (2017); p. 106 – 110;,
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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. 50594-82-6, name is 3,4,5-Trichlorobenzotrifluoride, This compound has unique chemical properties. The synthetic route is as follows., name: 3,4,5-Trichlorobenzotrifluoride

Example 1 : Preparation of a mixture comprising 1 ,3-dichloro-2-fluoro-5- trifluoromethylbenzene of the formula Il and 1 ,2-dichloro-3-fluoro-5- trifluoromethylbenzene of the formula III; 23 g (0.396 mol) KF, 12.8 g (0.03 mol) PPh4Br, 91.2 g sulfolane and 152 ml toluene were mixed in a 500 ml reactor. Toluene was distilled off under reduced pressure(1400C, thetaOmbar; aceotropic removal of water). After cooling to 1000C, 76 g (0.305 mol) 1 ,2,3-trichloro-5-trifluoromethylbenzene were added and the resulting mixture was heated at 190C for 15 h under reduced pressure (100 mbar). The mixture of 1 ,3- dichloro-2-fluoro-5-trifluoromethylbenzene and 1 ,2-dichloro-3-fluoro-5- trifluoromethylbenzene was distilled off simultaneously via a column. Two distillation fractions were obtained, which contained 31 % GC area-% of the product mixture, 1 % GC area-% of difluoro compounds and 6.6% GC area-% of the educt 1 ,2,3-trichloro-5- trifluoromethylbenzene. The identity of the mixture was determined by GC/MS spectrometry and 19F-NMR spectroscopy.

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 50594-82-6.

Reference:
Patent; BASF SE; WO2008/113660; (2008); 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. 39885-50-2, name is 2-Chloro-4-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-4-(trifluoromethyl)aniline

A mixture of 2-chloro-7- ( 1-ethylpropyl) -4-methoxy-l- methyl-ltf-benzimidazole (200 mg, 0.750 mmol) and 2-chloro- 4-trifluoromethylaniline (450 mg, 2.25 mmol) in l-methyl-2- pyrrolidone (0.5 mL) was stirred at 12O0C for 96 h under nitrogen atmosphere. The mixture was diluted with aqueous saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a 5-30percent ethyl acetate/n- hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from methanol to afford the title compound as colorless crystals(103 mg, 32percent) . mp 170-1710C.1H NMR (CDCl3) delta 0.85 t, J = 7.5 Hz, 6H), 1.60-1.85 (m, 4H), 3.15-3.20 (m, IH) 3.88 (s, 3H), 4.00 (s, 3H), 6.71 (d, J = 8.4 Hz, IH) , 6.85 (s, IH), 6.99 (d, J = 7.8 Hz, IH), 7.50 (d, J = 8.4 Hz, IH) , 7.65 (s, IH), 8.00 (d, J = 7.8 Hz, IH) .MS Calcd. : 425; MS Found: 426 (M+H) , 428.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/51533; (2008); A2;,
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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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

Step 15) 2-chloro-N-(5-methyl-lH-pyrazol-3-yl)pyrrolor2.1-/iri.2.41triazin-4-amine [0344] To a solution of 2,4-dichloropyrrolo[2, l- ][l,2,4]triazine (999.5 mg, 5.3 mmol) and 5- methyl-lH-pyrazol-3-amine (516.3 mg, 5.3 mmol) in EtOH (20 mL) was added Et3N (1.08 g, 10.7 mmol). After addition, the reaction mixture was stirred at rt overnight and concentrated in vacuo. The residue was beated with a mixture of H20 and EtOH (5/1 (v/v), 12 mL) at rt for 0.5 h and filtered. The filter cake was washed with PE (20 mL x 3) to give the title compound as a pale yellow solid (1.25 g, 94.7%). MS (ESI, pos. ion) m/z: 249.1 [M+H]+; ‘H NMR (600 MHz, DMSO-Jd): delta (ppm) 12.33 (s, 1H), 11.01 (s, 1H), 7.74 (s, 1H), 7.34 (s, 1H), 6.70 (s, 1H), 6.54 (s, 1H), 2.27 (s, 3H).

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; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; LI, Minxiong; HU, Haiyang; DAI, Weilong; LI, Xiaobo; WANG, Tingjin; WU, Yanjun; (136 pag.)WO2016/190847; (2016); A1;,
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Related Products of 13726-14-2,Some common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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: Procedure B: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below.

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

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
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14862-52-3, name is 3,5-Dibromochlorobenzene, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 3,5-Dibromochlorobenzene

General procedure: To degassed DMF (8.0 mL) was added Pd(dppf)Cl2 (73 mg, 0.10 mmol), bis(pinacolato)diboron (508 mg, 2.0 mmol), potassium acetate (589 mg, 6.0 mmol), and 2,6-dibromobenzene (0.121 mL, 236 mg, 1.0 mmol) in order at room temperature. The mixture was heated to 130 C for 1 hour to complete formation of the boronic ester. Then 3-bromopyridine (0.289 mL, 474 mg, 3.0 mmol) and degassed aqueous sodium hydroxide (2.00 mL, 3.0 M, 6.0 mmol) were sequentially added to the hot reaction, and heating at 130 C was continued for another 3 hours when the reaction was complete (by GCMS). The reaction was cooled and evaporated to a residue in vacuo. The residue was extracted with chloroform, and the combined extracts were concentrated and applied to preparative silica TLC plates. After development by 1:1 THF:EtOAc the product bands were removed and extracted with DME. Evaporation of extract solutions resulted in the yields. The products could be purified by sublimation at 180 C and 10 mmHg if needed.

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

Reference:
Article; Avitia, Bertoldo; MacIntosh, Eric; Muhia, Samuel; Kelson, Eric; Tetrahedron Letters; vol. 52; 14; (2011); p. 1631 – 1634;,
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