Category: chlorides-buliding-blocks

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.

Comparative Example 7 Preparation of 3,5-difluorochlorobenzene by reaction of 1,3,5-trichlorobenzene using tetrakis(diethylamino)phosphonium bromide as catalyst. 180 g (1 mol) of 1,3,5-trichlorobenzene, 114 g (2 mol) of potassium fluoride and 7.98 g (0.02 mol) of tetrakis(diethylamino)phosphonium bromide are used and the procedure described in Example 4 is employed.

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

Reference:
Patent; Aventis Research & Technologies GmbH & Co. KG; US6103659; (2000); A;,
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108-70-3, 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. 108-70-3, name is 1,3,5-Trichlorobenzene, A new synthetic method of this compound is introduced below.

This is an example of the coupling addition of three aryl groups to a trichloro aromatic hydrocarbon by the catalyst of this disclosure. [0071] The 1 liter coupling reaction flask was equipped as described inexample 3. The flask was charged with anhydrous NiBr2 0.55 grams / 2.5 mmole, TPP 6.55 grams / 25 mmole; 1,3,5-trichlorobenzene 18.31 grams / 0.10 mole and 50 ml / 44.3 grams of reagent grade o-xylene. The green solution of the NiBr2/TPP catalyst was formed by heating the mixture to ref lux and holding at reflux for 30 minutes. After cooling to ambient temperature, 100 ml of dry THE solvent was added. The 500 ml pressure equalizing addition funnel was charged with 320 ml of 1 .0 molar 2-chloromagnesiumtoluenesolution in THE (Aldrich) 0.32 mole. This represents a 3.2/ 1 mole ratio of Grignard / trichloroaryl or about a 7 mole % excess of Grignard. A sample of the starting mixture was taken for gas chromatographic analysis (sample 1). [0072] The coupling reaction was carried out at 50 degrees Celsius by the dropwize addition of the Grignard reactant over 2 hours and 50 minutes.The addition of the Grignard solution turned the mixture to a red-brown color. The mixture was stirred an additional 2 hours at 50 degrees Celsius following the complete addition of the Grignard. Additional samples were taken at 41% of the Grignard addition (sample 2); immediately following the complete addition of Grignard (sample 3); after 2 hours of additional stirring (sample 4)and following the acid hydrogen peroxide quench (sample 5). The table below lists the amount in grams of a given material in the reaction flask on the basis of gas chromatographic analysis. Sample 5 was also submitted for GC-MS analysis for identification of the individual components. This analysis was unable to find any traces of the mono-arylation intermediate product, atestament to the efficiency of the catalyst of this disclosure to poly-arylate multihalogenated aromatic compounds. [0073] The crude product solution was treated with 35 ml of concentrated hydrochloric acid and 115 ml of deionized water, followed by the addition of 3 ml of 50% aqueous hydrogen peroxide. The two liquid phases were separated in a funnel and the yellow organic layer was washed with two 100 ml portionsof 1% aqueous NaCI solution. The organic layer was subjected to nitrogen stripping followed by vacuum at 0.5 kPa pressure while warming the flask to about 50 degrees Celsius to remove all the THE and most of the o-xylene. The sticky solid was dissolved in a mixture of 200 ml of isomeric hexane and 50 ml of toluene. This was passed through a 2.5 cm by 7.5 cm diameter bed ofBrockmann I alumina and the bed washed through with a total of 300 ml of a2/1 v/v mixture of isomeric hexane / toluene. The clear colorless filtrate was stripped with nitrogen to a white sticky waxy solid. This material was recrystallized from 100 ml of refluxing isomeric hexane and cooling to ambient temperature. The white crystals were washed with two 25 ml portions of coldisomeric hexane and dried under 0.5 kPa vacuum. The net weight of pure product was 21.14 grams representing 60% theoretical yield based on 1,3,5- trichlorobenzene.[0074] The proton NMR spectrum ppm relative to TMS: 3H (S) 7.31 ppm 2,4,6 aromatic C-H; 12H (overlapping doublets) 7.30-7.32 ppm aromatic C-Hon outside aromatic rings; 9H (S) 2.415 ppm benzylic CH3.

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; EASTMAN CHEMICAL COMPANY; DEVON, Thomas, James; (41 pag.)WO2018/44824; (2018); A1;,
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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. 1871-57-4

Step 2: ((2-(chloromethyl)allyloxy)methyl)benzeneTo an over-dried flask was added DME (240 mL), sodium hydride (4.12 g, 120 mmol), and then benzyl alcohol (12.4 mL, 120 mmol) was added dropwise. After the addition was complete the mixture was heated to reflux for 1 hour. The mixture was cooled to 0 C in an ice-water bath and 3-chloro-2-(chloromethyl)prop-1-ene (12.7 mL, 120 mmol) was added in one portion. The mixture was heated to reflux for 19 hours, cooled to room temperature, and poured into saturated sodium hydrogen carbonate solution (250 mL). The aqueous layer was extracted with diethyl ether (4×200 mL). The combined organic layers were dried with anhydrous sodium sulphate, filtered, and concentrated in vacuo to give a residue which was fractionated to give ((2-(chloromethyl)allyloxy)methyl)benzene (10.7 g, 45.5%) as a colorless oil. LCMS (m/z, ES+) = 219 (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 1871-57-4, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; JOHNS, Brian Alvin; SHOTWELL, John Brad; HAIGH, David; WO2012/67663; (2012); A1;,
Chloride – Wikipedia,
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108-41-8, name is 1-Chloro-3-methylbenzene, 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. 108-41-8

General procedure: Under an N2atmosphere, KOtBu (1.3 mmol), complex 1 (1 mol%),dioxane (2 ml), amines (1.3 mmol) and aryl chlorides (1.0 mmol)were successively added into a Schlenk tube. The mixture wasstirred vigorously at 90C for 4 h. Then the solvent was removedunder reduced pressure and the residue was purified by columnchromatography on silica gel (eluent:PE/EA = 15:1) to give the pureproducts. The reported yields are the average of two runs.The catalytic reactions have been given in Tables 4-7. The result-ing amines were identified by comparison of the1H and13C NMRdata with those previously reported (ESI).

Statistics shows that 108-41-8 is playing an increasingly important role. we look forward to future research findings about 1-Chloro-3-methylbenzene.

Reference:
Article; Nirmala, Muthukumaran; Prakash, Govindan; Ramachandran, Rangasamy; Viswanathamurthi, Periasamy; Malecki, Jan Grzegorz; Linert, Wolfgang; Journal of Molecular Catalysis A: Chemical; vol. 397; (2015); p. 56 – 67;,
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60811-21-4, A common compound: 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

In a microwave vial equipped with a stir bar, 4-bromo-2-chloro-1-fluorobenzene (1 equiv, Combi-Blocks, CAS 60811-21-4), oxetan-3-ol (10 equiv) and Cs2CO3 (1 equiv) were combined. The vial was sealed, degassed and heated to 120 C. for 20 hours in an oil bath. The reaction mixture was purified by reverse-phase column chromatography using a C18 cartridge on an automated Teledyne ISCO Rf machine, eluting with 10% to 100% acetonitrile in water+0.1% formic acid as a gradient over 20 minutes. The fractions containing the desired compound were combined and concentrated under vacuum to provide the title compound

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-2-chloro-1-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tempest Therapeutics, Inc.; BRAVO, Yalda; CHEN, Austin Chih-Yu; DING, Jinyue; GOMEZ, Robert; LAM, Heather; NAGAMIZO, Joe Fred; OBALLA, Renata Marcella; POWELL, David Andrew; SHENG, Tao; (190 pag.)US2019/315712; (2019); A1;,
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6579-54-0, The chemical industry reduces the impact on the environment during synthesis 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, I believe this compound will play a more active role in future production and life.

171 mg 3-[6-(2-Methoxy-phenyl)-pyrimidin-4-ylamino]-benzyl-ammonium chloride (prepared in Example 69) (0.5 mmol) was dissolved in 50 cm3 dry dichloromethane, 0.350 cm3 N,N-diisopropyl-ethylamine (259 mg, 2 mmol) was added and the mixture was cooled to 0 C. in an ice bath. After stirring it for 15 minutes 196 mg 2,6-dichlorobenzenesulfonyl-chloride (0.8 mmol) was added and the mixture was stirred for 2 hours at 0 C. and overnight at room temperature. Then 50 cm3 5% NaHCO3 solution was added and it was extracted three times with 50-50 cm3 of chloroform. The combined organic layer was washed with brine, dried over MgSO4, decolorized with activated carbon and evaporated under reduced pressure. The residual solid was recrystallized from minimal amount of acetonitrile and air-dried to give the desired product as an yellow solid. Yield: 34 mg (13%). For analitical results and compound identification see Table 1.

The chemical industry reduces the impact on the environment during synthesis 2,6-Dichlorobenzenesulfonyl chloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Greff, Zoltan; Varga, Zoltan; Keri, Gyoergy; Nemeth, Gabor; Oerfi, Laszlo; Szantai Kis, Csaba; US2012/258968; (2012); A1;,
Chloride – Wikipedia,
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Adding some certain compound to certain chemical reactions, such as: 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, 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 104-11-0. 104-11-0

1-Benzyl-3-(4-chloro-phenyl)-3-methyl-1-{1-[5-methyl-2-(4-trifluoromethyl-phenyl)-1H-imidazol-4-ylmethyl]-piperidin-4-yl}-urea A solution of p-chloro-N-methylbenzylamine (282 mg) in dichloromethane (10 ml) was treated with pyridine (0.96 ml) followed by a solution of 20% phosgene in toluene (3.1 ml) and stirred at ambient temperature for 16 h. The mixture was quenched by the addition of saturated sodium hydrogen carbonate (10 ml), and the organic layer was en separated, dried (anhydrous magnesium sulphate), filtered and evaporated under reduced pressure. The residue was dissolved in dichloromethane (10 ml) and a solution of N-benzyl-1-[[2-[4-(trifluoromethyl)phenyl]-5-methyl-1H-imidazol-4-yl]methyl]-4-piperidinamine (657 mg) in dichloromethane (10 ml) was added followed by more pyridine (0.96 ml) and the mixture stirred for a further 16 h. The mixture was diluted with dichloromethane (40 ml) followed by brine (2*20 ml). The organic layer was separated, dried (anhydrous magnesium sulphate), filtered and evaporated under reduced pressure. The residue was purified by flash chromotography eluding with 10% methanol in dichloromethane to give the title compound (512 mg, 56%). Mass spectrum 597 [M+H]+.

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 1-(4-Chlorophenyl)-N-methylmethanamine.

Reference:
Patent; Edlin, Christopher David; Redshaw, Sally; Smith, Ian Edward David; Walter, Daryl Simon; US2003/69276; (2003); A1;,
Chloride – Wikipedia,
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13726-14-2, A common compound: 13726-14-2, name is 4-Chloro-3-methoxyaniline, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Step 3. 2-Chloro-N-(4-chloro-3-methoxyphenyl)-acetamideChloroacetyl chloride (10 mmol) is added dropwise to a mixture of 4-chloro-3-methoxyaniline (1.57 g, 10 mmol), ethyl ether (30 mL) and NaHCO3 (saturated solution, 30 mL) at room temperature and under vigorous stirring. After 1 h at room temperature the layers are separated, the organic layer is washed with NaHCO3 (saturated solution, 2×30 mL), brine (2 x 30 mL), aqueous HC1 (1M, 30 mL), and brine (2 x 30 mL), and dried (MgSO4). The solvent is removed under reduced pressure to produce the title compound as an off-white solid. H-l NMR: 3.91 (s, 3H); 4.18 (s, 2H); 6.90 (dd, 1H); 7.30 (d, 1H); 7.46 (d, 1H); 8.22 (broad, 1H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Chloro-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROGEN CORPORATION; WO2006/15279; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

627-42-9, A common heterocyclic compound, 627-42-9, name is 2-Methoxyethyl chloride, molecular formula is C3H7ClO, 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.

p-Acetylphenol (20.0 g, 147 mmol) was dissolved in DMF (200 mL). While cooling on ice, sodium hydride (6.46 g, 0.16 mol, 60% in oil) and then chloromethyl methylether (16.7 mL, 220 mmol) were added to the solution, and the mixture was stirred for 2 hours at the same temperature. The reaction solution was added with ice and saturated aqueous sodium hydrogencarbonate, and extracted with ethyl acetate. After the organic layer was washed with saturated brine, the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was,purified by silica gel column chromatography (n-hexane/ethyl acetate = 9/1), and 4-(methoxymethoxy)acetophenone (23.7 g, 89% yield) was obtained. FAB -MS m/z: [M+H]+ 181.1H-NMR (CDCl3) delta (ppm): 2.56 (s, 3H), 3.48 (s, 3H), 5.23 (s, 2H), 7.07 (d, J = 9.1 Hz, 2H), 7.93 (d, J = 9.1 Hz, 2H).

The synthetic route of 627-42-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kogyo Co., Ltd; EP1431280; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 108-41-8, name is 1-Chloro-3-methylbenzene, 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 108-41-8. 108-41-8

General procedure: (If aryl chloride is liquid) under N2 atmosphere, arylboronic acid 3 (0.6 mmol), 1a (1.0 mol%), K3PO4¡¤3H2O (2.0 equiv), H2O (2.0 mL), and THF (1.0 mL) were added into a Schlenk reaction tube, then aryl chloride 2 (0.5 mmol) was added. The mixture was stirred at room temperature for 24 h. Then the mixture was extracted with EtOAc, dried over anhydrous Na2SO4, filtered and purified by flash column chromatography to give the pure products.Comment(If aryl chloride is solid) under N2 atmosphere, aryl chloride 2 (0.5 mmol), arylboronic acid 3 (0.6 mmol), 1a (1.0 mol%), K3PO4¡¤3H2O (2.0 equiv), H2O (2.0 mL), and THF (1.0 mL) were added into a Schlenk reaction tube. The mixture was stirred at room temperature for 24 h. Then the mixture was extracted with EtOAc, dried over anhydrous Na2SO4, filtered and purified by flash column chromatography to give the pure products.

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 1-Chloro-3-methylbenzene.

Reference:
Article; Tang, Yi-Qiang; Lu, Jian-Mei; Shao, Li-Xiong; Journal of Organometallic Chemistry; vol. 696; 23; (2011); p. 3741 – 3744;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics