Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 14862-52-3, name is 3,5-Dibromochlorobenzene, 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 14862-52-3, COA of Formula: C6H3Br2Cl

Synthesis of Intermediate I-6 (0251) 1,3-dibromo-5-chlorobenzene (100 g, 370 mmol) was dissolved in THF (2 L) in a nitrogen environment, phenylboronic acid (47.3 g, 388 mmol) and tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (1.5 g, 1.36 mmol) were added thereto, and the mixture was stirred. Potassium carbonate (K2CO3) (127 g, 925 mmol) saturated in water was added thereto, and the resulting mixture was heated and refluxed at 80 C. for 12 hours. When the reaction was complete, water was added to the reaction solution, the mixture was extracted with dichloromethane (DCM), and an extract therefrom was filtered and concentrated under a reduced pressure after removing moisture with anhydrous MgSO4. The obtained residue was separated and purified through flash column chromatography to obtain an intermediate I-6 (49 g, 50%). (0252) HRMS (70 eV, EI+): m/z calcd for C12H8BrCl: 265.9498, found: 266 Elemental Analysis: C, 54%; H, 3%

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

Reference:
Patent; SAMSUNG SDI CO., LTD.; OH, Jaejin; KANG, Giwook; KANG, Eui Su; KIM, Youngkwon; KIM, Younhwan; KIM, Hun; PARK, Jaehan; YU, Eun Sun; JUNG, Ho Kuk; CHO, Pyeongseok; (174 pag.)US2017/98778; (2017); 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. 622-86-6, name is (2-Chloroethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H9ClO

3- Bromophenylacetic acid (4.0 g, 18.6 mmol) was dissolved in trifluoroacetic anhydride (3.6 mL, 25.9 mmol), then (2-chloroethoxy)benzene (2.56 mL, 18.6 mmol) was added dropwise. The resulting mixture was allowed to stir at room temperature overnight. The reaction mixture was quenched with saturated aqueous sodium bicarbonate solution and then extracted twice with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate and then concentrated on a rotary evaporator. The resulting residue was purified by chromatography on silica gel to afford the desired product (5.46 g, 83% yield) as a yellow solid. NMR (400 MHz, MeOD) delta 8.07 (d, J =8.9 Hz, 2H), 7.47-7.40 (m, 2H), 7.25-7.24 (m, 2H), 7.07(d, J = 8.9 Hz, 2H), 4.37-4.33 (m, 4H), 3.92-3.89 (m, 2H); MS (ESI) (m/z) 355 (M+H)+. (0862)

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 622-86-6.

Reference:
Patent; TEMPLE UNIVERSITY-OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; CHILDERS, Wayne, E.; ABOU-GHARBIA, Magid; JACOBSON, Marlene, A.; FAN, Rong; MARTINEZ, Rogelio, L.; MELENSKI, Edward, George; (126 pag.)WO2017/205451; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 50638-46-5, name is 4-Bromo-3-chloroanisole, 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 50638-46-5, HPLC of Formula: C7H6BrClO

Step 1 Ethyl 2?-chloro-4?-methoxybiphenyl-2-carboxylate [0117] 1-bromo-2-chloro-4-methoxybenzene (44.3 g) was dissolved in toluene (220 ml), ethyl 2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoate (60.8 g), water (132 ml), sodium hydrogen carbonate (33.6 g) and dichlorobis(triphenylphosphine)palladium(II) (2.8 g) were added, and the mixture was stirred at an oil bath temperature of 120 C. for 7 hr. To the reaction mixture was added ethyl 2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoate (5.2 g), and the mixture was further stirred for 2 hr. The reaction mixture was cooled to room temperature, toluene (100 ml) and water (200 ml) were added, and the mixture was stirred overnight. To the reaction mixture was added activated carbon (3 g), and the mixture was further stirred for 1 hr. The insoluble material was filtered off through celite, and the insoluble material was washed with toluene (100 ml) and water (200 ml). The obtained filtrates were combined to allow for layer separation. The obtained organic layer was washed with water (100 ml), and the solvent was evaporated to give the title compound (67.7 g). [0119] 1H-NMR (400 MHz, DMSO-D6) delta: 7.88-7.86 (1H, m), 7.63 (1H, td, J=7.6, 1.4 Hz), 7.51 (1H, td, J=7.6, 1.4 Hz), 7.27 (1H, dd, J=7.6, 0.9 Hz), 7.18 (1H, d, J=8.6 Hz), 7.06 (1H, d, J=2.6 Hz), 6.95 (1H, dd, J=8.6, 2.6 Hz), 4.01 (2H, m), 3.80 (3H, s), 0.96 (3H, t, J=7.1 Hz).

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-3-chloroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MOTOMURA, Takahisa; MATSUO, Takuya; SHOMI, Gakujun; INOUE, Masafumi; US2015/25120; (2015); 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. 1303587-99-6, name is 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H6ClN3O

Synthesis of 8-benzyl-2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [I, 4] oxazine [0420] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine 1 (50 mg, 0.29 mmol) in DMF (0.25 mL) under argon atmosphere was added sodium hydride (35 mg, 0.87 mmol) at 0 C. After stirring for 5 mins, benzyl bromide (0.035 mL, 0.29 mmol) was added to the reaction mixture at RT and stirred for 2 h. After consumption of the starting materials (monitored by TLC), the reaction was diluted with water (10 mL) and extracted with 5% MeOH/ CH2CI2 (2 x 5 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 2% MeOH: CH2CI2 to afford 8-benzyl-2-chloro-7, 8-dihydro- 6H-pyrimido [5, 4-b] [1, 4] oxazine (75 mg, 98%) as an off-white solid. 1H-NMR (DMSO-<, 400 MHz): delta 7.70 (s, 1H), 7.33-7.21 (m, 5H), 4.78 (s, 2H), 4.20-4.17 (m, 2H), 3.50-3.48 (m, 2H); LCMS: 262.3 (M+l); (column; X-Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 4.10 min. 0.05% Aq TFA: ACN; 0.80 mL/min); TLC: 5% MeOH/ CH2C12 (R 0.7). According to the analysis of related databases, 1303587-99-6, the application of this compound in the production field has become more and more popular. Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 13526-66-4, 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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows.

13.9 g (59.8 mmol) 3-bromo-6-chloro-imidazo[1 ,2-b]pyridazine were suspended in 508 mL 1 ,4-dioxane. 10.1 g (62.8 mmol) 2-benzofuranylboronic acid, 2.76 g (2.29 mmol) tetrakis(tn’phenylphosphino)palladium-(0) and 19.0 g (179 mmol) sodium carbonate were added. The obtained mixture was heated to 100C for 24 h. 400 mL of a saturated aqueous ammonium chloride solution were added. The obtained mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the obtained solid material was digested in 40 mL of a mixture of dichloromethane and methanol (8:2), filtered off and dried in vacuo to yield 5.42 g (44%) of the title compound as solid material. 1H-NMR (300MHz, DMSO-d6): delta [ppm]= 7.23 – 7.40 (m, 2H), 7.51 (d, 1 H), 7.59 – 7.67 (m, 2H), 7.77 (d, 1 H), 8.33 – 8.40 (m, 2H). LCMS (Method 1 ): Rt = 1.35 min; MS (ESIpos) m/z = 270 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-6-chloroimidazo[1,2-b]pyridazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; EIS, Knut; PUeHLER, Florian; ZORN, Ludwig; SCHOLZ, Arne; LIENAU, Philip; GNOTH, Mark, Jean; BOeMER, Ulf; GUeNTHER, Judith; WO2013/41634; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2687-12-9, 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. 2687-12-9, name is Cinnamyl chloride, This compound has unique chemical properties. The synthetic route is as follows.

Representative experimental procedure for carboxylative coupling reaction Taking the carboxylative coupling of 4-methylphenylacetylene, cinnamyl chloride (2a), and CO2 as example: A 70 mL oven dried autoclave containing a stir bar was charged with AgI (0.5 mg, 0.002 mmol) and Cs2CO3 (978 mg, 3.0 mmol). 4-Methylphenylacetylene (232 mg, 2.0 mmol), cinnamyl chloride (458 mg, 3.0 mmol), and 20 mL dry DMF were added with syringe, respectively, after purging the autoclave with CO2 three times. The sealed autoclave was pressurized to appropriate pressure with CO2. The reaction mixture was stirred at 60 C for 24 h, then the autoclave was cooled to room temperature and the remaining CO2 was vented slowly. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (3*30 mL). The combined organic layers were washed with water and brine, dried over Na2SO4, and filtered. The solvent was removed under vacuum. The product (E)-cinnamyl 4-methylphenylpropiolate (3b) (502 mg, 1.82 mmol, 91% yield) was isolated by column chromatography on silica gel (ethyl acetate/petroleum ether: 1:25).

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

Reference:
Article; Zhang, Xiao; Zhang, Wen-Zhen; Shi, Ling-Long; Zhu, Chuang; Jiang, Jiao-Lai; Lu, Xiao-Bing; Tetrahedron; vol. 68; 44; (2012); p. 9085 – 9089;,
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. 56131-47-6, name is 1-Bromo-2-chloro-3-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-2-chloro-3-(trifluoromethyl)benzene

l-Bromo-2-chloro-3-trifluoromethyl-benzene D-I-Ia (4.9 g, 18.9 mmol) is taken up in cone, sulphuric acid (20 mL), cooled to 0 0C and combined with an ice-cold mixture of cone, nitric acid (25 mL) and cone, sulphuric acid (20 mL). After 3 h stirring at RT the reaction mixture is poured onto ice water, extracted with EtOAc, the organic phase is washed with sat. NaHCO3 solution and sat. NaCl solution, dried on Na2SO4, filtered and evaporated down using the rotary evaporator and the intermediate product Z-9a obtained (HPLC-MS: tRet. = 2.14 min) is further reacted directly.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/3999; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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;,
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. 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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics