Tag: M.W=200-300

Electric Literature of 19752-55-7,Some common heterocyclic compound, 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, molecular formula is C6H3BrCl2, 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 5.1 g (0.209 mol) of magnesium turnings were added 0.45 g of a 1 molar solution of DIBAL in hexane at 60°C. After 15 min, 3,5-dichloro-bromobenzene (5.0 g, 0.022 mol) and 25 mL THF were added and the mixture was stirred. After start up of the reaction a mixture of 45g (0.2 mol) 3,5-dichloro-bromobenzene and 250 mL THF was added under reflux. After completion of the reaction the mixture was cooled to 0°C and 31 .1 g (0.219 mol) of ethyl trifluoroacetate were added. After 2 h an aqueous solution of NH4CI was added and the mixture was separated between MTBE and aqueous N H4CI solution. The organic layer was separated and the solvent was removed in vacuum. (34.3g brown oil; purity 70percent acc. to g.c; yield 50percent)1H-NMR (360 MHz, CDCI3): delta = 7.7 (s, 1 H), 7.9 (s, 2H) ppm.

The synthetic route of 19752-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; KOeRBER, Karsten; KORDES, Markus; RACK, Michael; VON DEYN, Wolfgang; KAISER, Florian; WO2012/59441; (2012); A2;,
Chloride – Wikipedia,
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Application of 39226-96-5, A common heterocyclic compound, 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, molecular formula is C8H7ClF3N, 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.

Example 59 N-{[2-Chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-1-(1-methyl- 1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxamide (E59) (in a form obtainable or prepared from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4-imidazolidinecarboxylic acid); A solution of 3-methyl-1-(1-methyl-1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylic acid (166 mg, 0.517 mmol) and N-ethyl morpholine (0.397 ml, 3.10 mmol) in dichloromethane (5 ml) was treated with 1-hydroxybenzotriazole hydrate (95 mg, 0.620 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (99 mg, 0.517 mmol) and stirred at room temperature for 10 minutes. 1-[2-Chloro-3- (trifluoromethyl)phenyl]methanamine (108 mg, 0.517 mmol) was then added and the reaction stirred overnight at room temperature. The reaction mixture was diluted with dichloromethane and washed with saturated sodium hydrogen carbonate solution, water and brine, separated through a hydrophobic frit and the organic layer was reduced under vacuum. The residue was purified by mass-directed automated HPLC to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-1-(1-methyl-1 H- imidazol-2-yl)-2-oxo-4-imidazolidinecarboxamide (67 mg, 29.6 % yield). LC/MS [M+H]+ = 416, retention time = 1.89 minutes.

The synthetic route of 39226-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
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. 60811-18-9, name is 4-Bromo-1-chloro-2-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3BrClF

EXAMPLE 219 (+)-(4aR)-(10bR)-4-methyl-8-(4-chloro-3-fluorophenyl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one STR237 A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one-8-boronic acid (178 mg, 0.65 mmol), tetrakis(triphenylphosphine)palladium(0) (23 mg, 0.02 mmol), 1-bromo-4-chloro-3-fluorobenzene (136 mg, 0.65 mmol), 0.65 mL of 2M sodium carbonate and 2 mL of THF, fitted with a reflux condenser, and the stirred mixture was heated at 80, under nitrogen, for 24 h. The mixture was cooled, diluted with ethyl acetate (75 mL) and washed with brine (2*25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (ethyl acetate eluent) to give 125 mg (56%) of the title compound as an amorphous foam. FDMS: m/e=357. alpha[D]589 =+74.28 (c=0.35, chloroform).

According to the analysis of related databases, 60811-18-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eli Lilly and Company; US5578724; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, molecular formula is C6H3BrClF, 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. category: chlorides-buliding-blocks

(First step) Preparation of 2-(3-chloro-5-fluorophenyl)-5-pentylpyrimidine A solution of 3-chloro-5-fluorophenylmagnesium bromide [prepared from 22.7 g (108.3 mmol) of 3-chloro-5-fluoro-bromobenzene and 2.7 g (111.0 mmol) of magnesium, and 100 ml of diethyl ether] in diethyl ether was added by drops to a mixture of 10 g (54.1 mmol) of 2-chloro-5-pentylpyrimidine, 0.4 g (0.5 mmol) of dichloro[1,1′-bis(diphenylphosphino) ferrrocene]palladium, and 300 ml of diethyl ether while being maintained at a temperature lower than -60 C., stirred at the same temperature for 1 hour, and then stirred at 10 C. for 10 hours. A diluted hydrochloric acid in an amount of 300 ml was added to the reaction mixture and extracted with 250 ml of heptane. The organic layer thus obtained was washed with a diluted aqueous sodium bicarbonate solution thrice and water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure and the residue was subjected to silica gel column chromatography (eluent: heptane/toluene=1/1) to obtain 11.0 g of a crude 2-(3-chloro-5-fluorophenyl)-5-pentylpyrimidine. (Yield: 72.8%) This product was used for the subsequent reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33863-76-2, its application will become more common.

Reference:
Patent; Chisso Corporation; US6329027; (2001); B1;,
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. 38762-41-3, name is 4-Bromo-2-chloroaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 38762-41-3

General procedure: Method A: To a solution of 3a (150 mg, 0.47 mmol) in a mixture of dry DME (3 mL) and dry EtOH (3 mL), bis(triphenylphosphine)palladium(II) dichloride (17 mg, 0.02 mmol) was added. After 30 min, a solution of sodium carbonate (299 mg, 2.82 mmol) in H2O(2 mL) and a solution of 5-formyl-2-furanylboronic acid 4 (93 mg,0.66 mmol) in dry EtOH (1.5 mL) were added in this order. The reaction was heated under reflux for 12 h. After this time, H2O (4 mL)was added at 25 C and the organic phase was extracted with EtOAc(3 5 mL), dried over sodium sulfate, filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica gel (2% EtOAc in petroleum ether) to give 5a as orange solid(79 mg, 60%). Method B: To a suspension of 16a (1.0 g, 4.8 mmol) in H2O (20 mL), HCl (37%, 2 mL) was added. The resulting solution was cooled at 0 C and a solution of sodium nitrite (397 mg, 5.76 mmol) in H2O (2 mL) was added dropwise. After 1 h, a solution of 17(400 mL, 4.8 mmol) in acetone (2 mL) and solid copper(II) chloride(128 mg, 0.96 mmol) were added. The mixture kept at 25 C for 12 h. EtOAc was added (3 10 mL) and the organic phase was separated, dried over sodium sulfate, filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica gel (2% EtOAc in petroleum ether) to give 5a as orange solid (1.23 g, 90%).

According to the analysis of related databases, 38762-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Vallone, Alessandra; D’Alessandro, Sarah; Brogi, Simone; Brindisi, Margherita; Chemi, Giulia; Alfano, Gloria; Lamponi, Stefania; Lee, Soon Goo; Jez, Joseph M.; Koolen, Karin J.M.; Dechering, Koen J.; Saponara, Simona; Fusi, Fabio; Gorelli, Beatrice; Taramelli, Donatella; Parapini, Silvia; Caldelari, Reto; Campiani, Giuseppe; Gemma, Sandra; Butini, Stefania; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 698 – 718;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, 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 19752-55-7, SDS of cas: 19752-55-7

EXAMPLE 2 27 Grams of powdery magnesium (purity 99.5percent) was dispersed in 200 ml of diethyl ether. A solution obtained by dissolving 226 g of 1-bromo-3,5-dichlorobenzene in 800 ml of diethyl ether was added dropwise to the dispersion heated at about 40° C., and after the addition, the mixture was stirred at the same temperature for 2 hours to react them whereby 3,5-dichlorophenylmagnesium bromide was produced.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3,5-dichlorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Ishihara Sangyo Kaisha Limited; US4230642; (1980); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 13918-92-8, 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 13918-92-8 as follows.

General procedure: To a mixture of 3-amino-2-methyl-thieno[2,3-d]pyrimidin-4(6H)-one (1.0 mmol) (8 and 9) and benzenesulfonyl chloride (1.1 mmol) in DCM (10 mL) was added dropwise pyridine (1.2 mmol) in dichloromethane (2 mL). The resulting mixture was stirred at room temperature for 12 hrs. The mixture was concentrated under reduced pressure, and theresidue was treated with water (30 mL). The aqueous mixture was neutralized by the addition of aqueous 10% HCl solution and extracted with DCM (230 mL). The organicphase was washed with aqueous saturated NH4Cl solution and brine. The organic layer was separated and dried over anhydrous MgSO4, filtered, and concentrated under reducedpressure to give the crude product, which was purified by silica gel chromatography to produce the pure corresponding compounds.

According to the analysis of related databases, 13918-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nie, Li Fei; Bozorov, Khurshed; Huang, Guozheng; Zhao, Jiangyu; Niu, Chao; Aisa, Haji Akber; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 193; 10; (2018); p. 656 – 667;,
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. 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 56961-77-4

EXAMPLE 10 6-(2,3-Dichlorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 109, structure 4 of Scheme II, where R1 =2,3-dichlorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9). From Compound 9 (68.0 mg, 0.21 mmol) and commercially available 2,3-dichlorobromobenzene (40.1 mg, 0.18 mmol, Lancaster) was obtained a crude product which was isolated and purified by reverse phase HPLC (ODS column, 97% methanol/water, 3.0 mL/min) to afford 20 mg (29%) of Compound 109. Data for Compound109: 1 H NMR (400 MHz, CDCl3)7.39 (dd, J=8, 1.6, 1H), 7.19 (dd, J=16.8, 1H), 7.23 (dd, J=4, 1.6, 1H), 7.11 (d, J=1.6, 1H), 7.05 (dd, J=8, 1.6, 1H), 6.46 (d, J=8, 1H), 5.34 (s, 1H), 3.82 (br s, 1H), 1.99 (s, 3H), 1.32 (s, 6H).

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

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5693646; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 19752-55-7, 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. 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 3,5-Dichloro-1-bromobenzene (7.46 g, 33.0 mmol) or 3,5-bis(trifluoromethyl)-1-bromobenzene (9.67 g, 33.0 mmol) was dissolved in ether (70 mL). To this solution, BuLi (1.58 M in hexane, 20.9 mL, 33.0 mmol) was added using syringe through septum cap at -78 °C for 20 min, and the mixture was stirred for 2 h at -78 °C. To the reaction mixture a solution of antimony (III) boromide (3.61 g, 10.0 mmol) in ether (50 mL) was added dropwise at -78 °C, and the resulting mixture was gradually raised to room temperature and stirred overnight. The reaction mixture was diluted with ether (150 mL) quenched with water. The mixture was extracted with ether (150 mL). The combined extracts were washed with brine and dried over anhydrous magnesium sulfate. The dried organic layer was concentrated under reduced pressure. The residue was purified on silica gel column chromatography to give 1n (hexane, 4.5 g, 80 percent yield) and 1o (hexane: CH2Cl2 4:1, 6.9 g, 91 percent yield).

The synthetic route of 1-Bromo-3,5-dichlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yasuike, Shuji; Nakata, Kazuhide; Qin, Weiwei; Matsumura, Mio; Kakusawa, Naoki; Kurita, Jyoji; Journal of Organometallic Chemistry; vol. 788; (2015); p. 9 – 16;,
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. 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

(b) into a 500mL three-neck bottle add 50g of compound 3, 50g of NBS (i.e. N-bromosuccinimide), 0.3g of BetaRho0 (i.e. dibenzoyl peroxide) and 300mL of carbon tetrachloride, the external temperature is raised at 90 C and the reaction is carried out for 24h (at this time, TLC showed complete reaction); pour the reaction solution into 500mL of ice water, adjust the pH at 10 with 2N (equivalent concentration) sodium hydroxide solution, layered extraction, combined organic phase, wash once with 5% sodium bicarbonate (mass concentration, the same below) solution, dry and then spin dry, separated by column chromatography and then obtained 52 g of compound 4 (yield is 75%)

The synthetic route of 27139-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liu Ke; (11 pag.)CN108409659; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics