Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 202865-57-4, name is 1-Bromo-2,5-dichloro-3-fluorobenzene, 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 202865-57-4, Safety of 1-Bromo-2,5-dichloro-3-fluorobenzene

6-chloro-2-fluoro-3-methylphenol (3.3 g, 20.55 mmol) and 18-crown-6 (1.086 g, 4.11 mmol) were dissolved in dry DMSO (50 ml.) and treated with 20% potassium t- butoxide in THF (1 1.50 g, 20.55 mmol) for 15 minutes at room temperature. 1- bromo-2,5-dichloro-3-fluorobenzene (7.21 g, 29.6 mmol) was added in one portion and the reaction mixture heated at 1 100C for 3 days at which time LC-MS indicated nearly complete consumption of phenol and formation of a major new product. Addition of water to the reaction mixture resulted in a brown gummy oil which was extracted with EtOAc. The organic phase was isolated, washed with brine four times, dried over MgSOphi filtered and concentrated to dryness to give a brown syrup. This material was filtered through a plug of 45 g silica gel which was eluted with 500 ml_ DCM. The filtrate was concentrated to an amber oil and crystallized from EtOH and a few drops of water. This mixture was cooled in an ice bath, filtered, and the precipitate washed with three portions of cold EtOH to give 2-[(3-bromo-2,5- dichlorophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene (4.0 g, 10.40 mmol, 50.6 % yield) as a cream solid. 1 H NMR (400 MHz, DMSO-c/6) delta ppm 7.73 (s, 1 H), 7.29 – 7.47 (m, 2 H), 6.81 (s, 1 H), 2.29 (s, 3 H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/154271; (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. 200190-87-0, name is 1-Bromo-4-chloro-2-fluoro-5-methylbenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-4-chloro-2-fluoro-5-methylbenzene

(2) Ether solution (45mmol) containing the compound prepared by the method of the Reference Example 9 (1) (3.15g, 14mmol) was stirred at -78?C, followed by dropwise addition of n-butyl lithium (1.6M in hexane, 10.2ml, 16mmol) over 10 minutes, and the stirring was continued at the same temperature for 30 minutes. Then, trimethyl borate (1.77g, 17mmol) in ether (8ml) was dropwise added at the same temperature over 10 minutes, and the resulting mixture was stirred for 3 hours at the same temperature. The temperature of the mixture was gradually increased to the room temperature by standing overnight. 1N hydrochloric acid (50ml) was added with ice cooling and the mixture was stirred at room temperature for 1 hour. The ether layer was separated, and the aqueous layer was extracted with ether. The ether layers were combined, washed with brine, dried and concentrated by evaporation of the solvent. A small amount of petroleum ether was added to the residue, followed by filtration of deposited crystals. The crystals were dried to obtain 4-chloro-2-fluoro-5-methylphenylboronic acid (2.94g). m.p.250-253?C 1H-NMR(DMSO-d6) delta 2.29(3H, s), 7.23(1H, d, J=8.8Hz), 7.50(1H, d, J=6.6Hz), 8.23(2H, br s) 19F-NMR(DMSO-d6) delta -106.1 IR(Nujol) 3360, 1608, 1568, 1235, 1132, 1045, 944, 795 cm-1

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; Sumitomo Chemical Takeda Agro Company, Limited; EP1333029; (2003); 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. 54773-20-5, name is 1,3-Dichloro-5-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Quality Control of 1,3-Dichloro-5-(trifluoromethyl)benzene

PREPARATION 1 1-(3-Chloro-5-trifluoromethyl-phenyl)-piperazine Beginning with 3,5-dichlorobenzotrifluoride (500 mg, 2.32 mmol) and piperazine (1 g, 11.6 mmol), 320 mg of the title compound was recovered by the procedure described in Example-1.

The synthetic route of 54773-20-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sonesson, Clas; Andersson, Bengt; Waters, Susanna; Waters, Nicholas; Tedroff, Joakim; US2003/4169; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 179897-90-6,Some common heterocyclic compound, 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, molecular formula is C6H2Br2ClF, 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 round bottom flask under nitrogen fitted with a stir bar was added 1- chloro-2,6-dibromo-4-fluorobenzene (14.36 g, 49.8 mmol), pivalamide (5.04 g, 49.8 mmol), cesium carbonate (21.09 g, 64.7 mmol) and dioxane (250 mL). The reaction mixture was sparged with nitrogen and Pd(dba)2 (1.43 g, 2.490 mmol) and 5-bis(diphenylphosphino)-9,9- dimethylxanthene (XANTPHOS, 2.02 g, 3.49 mmol) were added. The reaction was then sealed and heated in an oil bath at 70 C for 18 h. The reaction was allowed to cool to r.t and was partitioned between a saturated aqueous solution of NH4C1 and EtOAc. The layers were separated and the aqueous portion was extracted with EtOAc (2 X). The combined organic portions were washed with water, brine, dried (Na2S04), filtered, concentrated, and adsorbed onto silica gel. Purification by flash chromatography on silica gel using an EtO Ac- heptane (1-20%) elution gradient afforded N- (3-bromo-2-chloro-5-fluorphenyl)pivalamide (1 1.0 g, 33.8 mmol, 68 %) as a white crystalline solid. LCMS (m/z): 309.9 (MH+), tR = 1.1 1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-2-chloro-5-fluorobenzene, its application will become more common.

Reference:
Patent; NOVARTIS AG; MADERA, Ann Marie; POON, Daniel; SMITH, Aaron; WO2011/161216; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 121-27-7, These common heterocyclic compound, 121-27-7, name is 5-Chloro-2-(4-chlorophenoxy)aniline, 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.

A mixture of 43.6 g. of isonicotinic acid, 200 ml. of thionyl chloride and 200 ml. of methylene chloride is heated under reflux for 2 hours. The solvent is evaporated, 93.4 g. of 5-chloro-2-(p-chlorophenoxy)aniline, 180.0 g. of anhydrous potassium carbonate and 2800 ml. of benzene are added and the reaction proceeds as described in Example 1. Extraction with petroleum ether gives 5′-chloro-2′-(p-chlorophenoxy)-isonicotinanilide.

The synthetic route of 121-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US4221714; (1980); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 121-27-7, name is 5-Chloro-2-(4-chlorophenoxy)aniline, 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 121-27-7, Formula: C12H9Cl2NO

EXAMPLE IV-3 STR526 A solution of 27.6 g (0.4 mol) of sodium nitrite in 31.7 ml of water is added dropwise with stirring at 0 C. to 5 C. to 84.3 g (0.3 mol) of 5-chloro-2-(4-chlorophenoxy)aniline (compare, for example, EP No. 34,771), 284 ml of water and 72.2 ml of concentrated hydrochloric acid, the mixture is stirred for a further 15 minutes after completion of the addition and filtered, 16.4 g (0.2 mol) of sodium acetate are added to the filtrate and the solution thus obtainable is added dropwise with stirring at 10 C. to 15 C. to a mixture of 253 ml of water, 123 g (1.5 mol) of sodium acetate, 2.5 g (0.015 mol) of sodium sulphate, 15.9 g (0.1 mol) of copper(II) sulphate and 28.3 g (0.48 mol) of acetaldoxime. After completion of the addition, the mixture is stirred for one hour at room temperature, the pH is then adjusted to 7 by addition of about 40 ml of concentrated hydrochloric acid, 292 ml of concentrated hydrochloric acid are then added in portions and the mixture is heated to reflux temperature for 3 hours. The reaction mixture is subjected to a steam distillation, the oil which separates is taken up in dichloromethane, and the solution is dried over sodium sulphate, concentrated and distilled in a high vacuum. 29.5 g (35% of theory) of 5-chloro-2-(4-chlorophenoxy)acetophenone of boiling point 80-85 C. at 1.5 mbar are obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-2-(4-chlorophenoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Aktiengesellschaft; US4956370; (1990); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 445-01-2,Some common heterocyclic compound, 445-01-2, name is 4-Bromo-1-chloro-2-(trifluoromethyl)benzene, molecular formula is C7H3BrClF3, 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.

PREPARATION 4 1-Benzyl-4-(4-chloro-3-trifluoromethyl-phenyl)-piperidine-4-ol (Prepared according to Collection Czechoslav. Chem. Commun. 1973, 38, 3879) A solution of 5-Bromo-2-chlorobenzotrifluoride (5 g, 19.2 mmol) in dry diethyl ether (40 ml) was added dropwise at room temperature to a mixture of Mg (470 mg) in dry diethyl ether (20 ml) under a stream of Argon (g). The reaction gave rise to a solution of Grignard’s reagent. A solution of 1-benzyl-4-piperidone (1.3 g, 6.88 mmol) in dry diethyl ether (30 ml) was added dropwise via syringe at room temperature. The combined mixture was stirred for 1 hour, and finally quenched with saturated ammonium chloride solution (40 ml). The mixture was extracted several times with EtOAc and the combined organic phases were dried (MgSO4), filtered and evaporated to dryness. The oily residue was chromathographed on a silica column using EtOAc:toluene (1:1 (v/v)) as eluent affording the title compound (1.6 g, 64%). MS m/z (relative intensity, 70 eV) 369 (M+, 23), 278 (15), 91 (bp), 65 (16), 56 (21).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-chloro-2-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; Sonesson, Clas; Andersson, Bengt; Waters, Susanna; Waters, Nicholas; Tedroff, Joakim; US2003/4169; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 1298031-94-3, A common heterocyclic compound, 1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, molecular formula is C7H5BrClN3, 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.

A dry three-necked round-bottomed flask at -78C under inert atmosphere was charged with anhydrous THF (20 mL). A solution of n-butyllithium (2.5 M in hexane, 26.1 mL, 65.3 mmol) was added dropwise, followed by addition of anhydrous acetonitrile (4 mL, 65.3 mmol). The internal temperature was maintained below -70 C during the entire addition process. After stirring 30 min at -78 C, a solution of 8-bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (2.0 g, 8.2 mmol, prepared according to Example 43) in anhydrous THF (20 mL) was added drop- wise. The mixture was stirred for 2 h at -78 C. The excess reagent was quenched carefully with sat’d aqueous NH4C1. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 0-35% EtOAc in petroleum ether to yield 2-(6-chloro- 2-methylimidazo[l,2-b]pyridazin-8-yl)acetonitrile (1.2 g, 71%). MS m/z 207.1, 209.1 [M+H]+.

The synthetic route of 1298031-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 320-50-3, 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 320-50-3 as follows.

Similarly, 4-(2-trifluoromethyl-4-chlorophenoxy)benzene is prepared by following the same procedure but using 1,4-dichloro-2-trifluoromethylbenzene in place of 1,2-dichloro-4-trifluoromethylbenzene.

According to the analysis of related databases, 320-50-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chevron Research; US4289909; (1981); A;,
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. 18112-31-7, name is 3-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H5BrClN3

A mixture of 50 mg (0.203 mmol) of 3-Bromo-6-chloro-2-methyl-imidazo[1 ,2-b]pyridazine (BKS422; preparation see Stage 61.1 ), 92 mg (0.446 mmol) of (4-methylsulfonyl)- EPO phenylboronic acid (Combi-Blocks), 0.51 ml of a aqueous 1 M K2CO3-solution, 8 mg of Pd(PPh3)2CI2 in 1.5 ml of DMF are heated in an oil bath at 1050C for 5 h. The reaction mixture is ppured into CH2CI2, washed with water and dried (Na2SO4). After the solvent is evaporated, the residue is purified by chromatography on silicagel. Solvent system: CH2CI2- EtOAc = 100-0 (start) to 0/100 (end). The title compound is isolated as a yellow solid. MS: 442 (M+1 ); HPLC: tR = 3.71 Omin.

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 18112-31-7.

Reference:
Patent; NOVARTIS AG; WO2008/52733; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics