Tag: M.W=200-300

328-84-7, 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. 328-84-7, name is 3,4-Dichlorobenzotrifluoride, This compound has unique chemical properties. The synthetic route is as follows.

(a) A mixture of 3,4-dichlorobenzotrifluoride (48 g), hydrazine hydrate (65 g) and pyridine (240 g) was stirred and heated at 150 C. for 6 hours in an autoclave at a pressure of 4 bar. The cooled mixture was quenched with sodium hydroxide solution and the organic layer evaporated in vacuo. The residue was dissolved in diethyl ether, washed (water) and the ether evaporated to give 2-chloro-4-trifluoromethylphenylhydrazine and 2-chloro-5-trifluoromethylphenylhydrazine as a 95/5 mixture (36 g),

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Reference:
Patent; Aventis CropScience, S.A.; US6410737; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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. 13526-66-4

13.9 g (59.8 mmol) 3-bromo-6-chloro-imidazo[l,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(triphenylphosphino)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. ^-NMR (300M HZ, DMSO-d6): delta [ppm] = 7.23 – 7.40 (2H), 7.51 (1H), 7.59 – 7.67 (2H), 7.77 (1H ), 8.33 – 8.40 (2H).LCMS (Method 1) : Rt= 1.35 min; MS (ESIpos) m/z = 270 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13526-66-4, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; PUeHLER, Florian; ZORN, Ludwig; SCHULZE, Volker; SUeLZLE, Detlev; LIENAU, Philip; WENGNER, Antje, Margret; PETERSEN, Kirstin; BOeMER, Ulf; WO2014/128093; (2014); A1;,
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96558-78-0, A common heterocyclic compound, 96558-78-0, name is 3-Bromo-5-chlorophenylamine, molecular formula is C6H5BrClN, 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.

To a solution of compound A (1 g, 4.8 mmol, 1 eq ), compound B (1.2 g, 7.3 mmol, 1.5 eq ) and K2CO3 (2.0 g, 14.5 mmol, 3 eq) in 5 mL of dioxane and 1 mL of H2O was added Pd(dppf)Cl2 (354.4 mg, 484.3 pmol, 0.1 eq) under N2. The mixture was stirred at 100C for 12 hours. Then it was partitioned between 30 mL of water and 60 mL of ethyl acetate. The organic phase was separated, washed with 30 mL of brine, dried over Na2SC>4, filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography (S1O2, eluting with a gradient of petroleum ether: ethyl acetate = 1 :0 to 1 : 1) to give 440 mg of compound C (2.6 mmol, 54.2% yield) as a brown oil.

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

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; VACCA, Joseph, P.; WAGER, Travis, T.; (383 pag.)WO2020/117877; (2020); A1;,
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Adding some certain compound to certain chemical reactions, such as: 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, 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 2770-11-8. 2770-11-8

Preparation of N-[2-(4-chlorophenoxy)phenyl]-3-acetamido-3-phenylpropanamide STX1858 C23H21ClN2O3, MW: 408.88 EPO To a pre-stirred solution of iV-acetyl-3-phenyl-beta-alanine (104 mg, 0.50 mmol), EDC (265 mg, 1.38 mmol), triethylamine (70 mg, 0.69 mmol) and DMAP (6 mg, 0.046 mmol) in anhydrous DCM (25 ml), was added 2-(4-chlorophenoxy)phenylamine (100 mg, 0.46 mmol). This mixture was then allowed to stir at room temperature for 14 h. The reaction mixture was washed with 2.5M NaOH (20 ml), 2M HCl (20 ml) and the organics were then dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (eluant; DCM to 9:1 DCM:MeOH) then proceeded to afford the desired product as an off-white solid (58.9 mg, 31%). 1H NMR (270 MHz, CDCl3): delta 2.03 (3H, s, CH3), 2.83-2.99 (2H, m, CH2), 5.30-5.40 (IH, m, CH), 6.73-6.77 (IH, dd, J= 1.5, 8.2 Hz, Ar-H), 6.83-6.86 (2H, m, Ar-H), 6.95-7.03 (IH, td, J= 1.7, 7.9 Hz, Ar-H), 7.05-7.11 (IH, td, J= 1.7, 7.9 Hz, Ar-H), 7.19-7.30 (7H, m, Ar-H), 7.60 (IH, br s, Ar-H), 8.22-8.25 ppm (IH, dd, J – 1.5, 8.0 Hz, Ar-H). LCMS: M+H: 409.44 HPLC: 98.66% (2.268 mins, isocratic 90% acetonitrile, 10% water at 1 rnl/min).

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 2-(4-Chlorophenoxy)aniline.

Reference:
Patent; STERIX LIMITED; WO2007/3934; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, 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 1996-30-1. 1996-30-1

Intermediate 7A. 3-Chloro-l-(5-chloro-2-fluorophenyl)propan-l-one: In a flame-dried 3 -neck flask, 2-bromo-4-chloro-l-fluorobenzene (2.0 g, 9.55 mmol) was dissolved in THF (anhydrous) (28.9 mL) under argon. Isopropylmagnesium chloride (2 M in THF) (5.01 mL, 10.03 mmol) was added, and the reaction was stirred at rt. To this solution was added zinc chloride (0.5 M in THF) (20.44 mL, 10.22 mmol) and the mixture was stirred at ambient temperature for 40 min. To the reaction was then added Pd(PPh3)4 (0.276 g, 0.239 mmol), and the mixture was cooled to 0 C. A solution of 3- chloropropanoyl chloride (0.981 mL, 10.22 mmol) in THF (2.89 mL) was added, and the reaction was stirred for 2 h at 0 C. The reaction mixture was then quenched with 3 N HCl, diluted with water, and extracted with Et20 (3x). The combined organics were dried (MgS04), filtered and evaporated to yield a grainy yellow liquid, which was purified using silica gel chromatography to obtain a colorless oil, 3-chloro-l-(5-chloro-2- fluorophenyl)propan-l-one (0.405 g, 19%). MS (ESI) m/z: 221.0 (M+H)+. 1H NMR (400 MHz, CDC13) delta 7.88 (dd, J = 6.3, 2.8 Hz, 1H), 7.51 (ddd, J = 8.8, 4.3, 2.8 Hz, 1H), 7.13 (dd, J = 10.2, 8.7 Hz, 1H), 3.94 – 3.88 (m, 2H), 3.46 (td, J = 6.6, 3.2 Hz, 2H) ppm.

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 3-Bromo-4-fluorochlorobenzene.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LAM, Patrick Y.S.; CLARK, Charles G.; CORTE, James R.; EWING, William R.; GILLIGAN, Paul J.; JEON, Yoon; YANG, Wu; SMITH, Leon, M., II.; WANG, Yufeng; WO2013/22814; (2013); A1;,
Chloride – Wikipedia,
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Some common heterocyclic compound, 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, molecular formula is C6H3Cl3O2S, 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. 6579-54-0

General procedure: To a solution of amine 7 (41 mg, 0.1 mmol) indry pyridine (2 mL), substituted benzenesulfonyl chloride (1.52 eq.) was added. The reaction mixturewas kept at r.t. overnight and poured into a mixture of 1 M hydrochloric acid (10 mL) and ethyl acetate(10 mL) while being vigorously stirred. The organic phase was separated and concentrated in vacuo.The residue was dissolved in a mixture of methanol (10 mL) and 5 M sodium hydroxide solution(5 mL) and kept at r.t. for 1 h. The mixture was concentrated in vacuo to remove the methanol andwas diluted with water (3 mL) and ltered. The clear water phase was washed with ethyl acetate(3 mL x 2) and then concentrated hydrochloric acid was added dropwise until pH = 4. The mixturewas filtered to afford the desired sulfonamide 9a-9n as yellow solids (yield: 30-80%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6579-54-0, its application will become more common.

Reference:
Article; Wang, Penghui; Jiang, Lulu; Cao, Yang; Ye, Deyong; Zhou, Lu; Molecules; vol. 23; 6; (2018);,
Chloride – Wikipedia,
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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. 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, A new synthetic method of this compound is introduced below., 6579-54-0

EXAMPLE 34; 2,6-dichloro-N-(2-chloro-5-(4-(4-morpholinyl)-6-quinolinyl)-3- pyridinyl)benzenesulfonamide; (Some starting materials may be obtained from Alfa Aesar, Ward Hills, MA) To a flame-dry 50 mL rb flask was added 2-chloro-5-(4-morpholinoquinolin-6-yl)pyridin-3-amine (0.07 g, 0.2 mmol) and THF (8 mL). The reaction mixture was cooled to 0 0C followed by adding sodium bis(trimethylsilyl)amide, 1.0m solution in tetrahydrofuran (0.4 ml, 0.4 mmol). After the addition, it was continued to stir at 0 0C under N2. After 30 min, 2,6-dichlorobenzene- 1-sulfonyl chloride (0.07 g, 0.3 mmol) was added into the reaction mixture. After the addition, it was continued to stir at 0 0C then slowly warmed up to rt overnight. The reaction was quenched with water. The solvent was concentrated. The residue was partitioned between EtOAc/water. The organic layer was washed with brine, dried over MgSO4 and concentrated. The crude product was purified using SiO2 (12 g) chromatography with DCM:EtOAc:MeOH=70%:26%:4% as the solvent system to afford the desired product as light yellow solid (63.0 mg). MS (ESI pos. ion) m/z: calc’d for C24H19Cl3N4O3S: 548.1; found: 549.4 (M+l). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 3.21 – 3.38 (m, 4 H) 3.93 – 4.11 (m, 4 H) 6.94 (d, J=4.97 Hz, 1 H) 7.33 – 7.44 (m, 1 H) 7.45 – 7.55 (m, 2 H) 7.85 (dd, J=8.77, 2.05 Hz, 1 H) 8.18 (d, J=8.77 Hz, 1 H) 8.25 (d, ./=1.90 Hz, 1 H) 8.39 – 8.50 (m, 2 H) 8.81 (d, J=4.97 Hz, 1 H).

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; AMGEN INC.; WO2009/155121; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, I believe this compound will play a more active role in future production and life. 60811-21-4

A mixture of 4-bromo-2-chloro-l-fluorobenzene (8.04 g) and sodium methylthiolate(3.05 g) in DMF (25 ml) was heated at 50 C for 2.5 h. Water was added and the mixture wasextracted with ether (three times). The organic extracts were washed with water (twice), dried(MgSO4), and evaporated to give the sub-title compound (8.93 g).1K NMR CDC13: 6 7.54 (1H, d), 7.34 (1H, dd), 7.02 (1H, dd), 2.47 (3H, s).

The chemical industry reduces the impact on the environment during synthesis 60811-21-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/21759; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1996-29-8, The chemical industry reduces the impact on the environment during synthesis 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, I believe this compound will play a more active role in future production and life.

Under argon atmosphere, a mixture of X-Phos (750 mg; 1.53 mmol), l-bromo-4-chloro-2-fluoro-benzene (1.93 mL; 15.31 mmol), ieri-butyl 4-[(4, 4,5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)methylene]piperidine- 1 -carboxylate (5 500 mg;, 15.31 mmol), Pd dba3 (708 mg; 0.76 mmol) and K3P04 (4 975 mg; 22.97 mmol) in a mixture of H20 (5 mL) and dioxane (100 mL) was heated to 100 C and stirred for 2 h. After cooling down to rt, H20 and EA were added. The organic layer was separated, washed with brine, dried over MgS04, filtered and concentrated to dryness. The residue was purified by column chromatography (silica gel;PE: EA; 30:1 ; v/v) to afford feri-butyl 4-[(4-chloro-2-fluoro-phenyl)methylene]piperidine-l- carboxylate (4 000 mg) as a white solid. (0255) MS xn/z (+ESI): 311.1, 313.1 [M-/-Bu+HCOOH]+. (0256) ?H-NMR (400 MHz, CDC13) d ppm: 7.10 – 7.06 (m, 3H), 6.20 (s, 1H), 3.51 (t, J= 5.6 Hz, 2H), 3.41 (t, J = 5.6 Hz, 2H), 2.36 – 2.30 (m, 4H), 1.48 (s, 9H).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-chloro-2-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BASILEA PHARMACEUTICA INTERNATIONAL AG; RICHALET, Florian; EL SHEMERLY, Mahmoud; LANE, Heidi; (43 pag.)WO2019/115709; (2019); A1;,
Chloride – Wikipedia,
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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. 64628-73-5, name is 3-Chloro-4-(trifluoromethoxy)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 64628-73-5

An ice-cold mixture of 98% H2SO4 (0.75 mL) and water (2.25 mL) was added to 3-chloro-4-(trifluoromethoxy)aniline (53) (1 .00 g, 4.73 mmol) and the resulting salt was crushed (using a glass rod) and cooled in an ice bath. A solution Of NaNO2 (359 mg, 5.20 mmol) in cold water (0.75 mL, then 0.25 mL) was added drop-wise, and the mixture was stirred at 0 0C for 12 min. A solution of urea (42.6 mg, 0.709 mmol) in cold water (0.25 mL) was added, and the mixture was stirred at 0 0C for 3 min. Finally, a solution of KI (1.65 g, 9.94 mmol) in cold water (1.6 mL, then 0.2 mL) was added slowly, and the mixture was stirred at room temperature for 10 min, and then at 52 C for 2 h. The resulting cooled mixture was diluted with ice-water (45 mL) and extracted with CH2Cl2 (4x 50 mL). The extracts were sequentially washed with an aqueous solution of Na2SO3 (30 mL of 0.5%) and then with water (40 mL) and finally concentrated carefully under reduced pressure at 17 C. The resulting oil was chromatographed on silica gel, eluting with pentane, to give 2-chloro-4-iodo- 1 -(trifluoromethoxy)benzene (54) (1.24 g, 81%) as a colourless oil (a white solid on freezing); 1H NMR (CDCl3) delta 7.82 (d, J = 2.1 Hz, 1 H), 7.61 (dd, J = 8.6, 2.1 Hz, 1 H), 7.05 (dq, J = 8.6, 2.0 Hz, 1 H); HRAPCIMS calcd for C7H3ClF3IO mlz (M+) 323.8834, 321.8864, found 323.8834, 321.8861.

The synthetic route of 64628-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT; DENNY, William, Alexander; THOMPSON, Andrew, M.; BLASER, Adrian; MA, Zhenkun; PALMER, Brian, Desmond; SUTHERLAND, Hamish, Scott; KMENTOVA, Iveta; WO2011/14774; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics