Chlorides-buliding-blocks

96558-78-0, 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. 96558-78-0, name is 3-Bromo-5-chlorophenylamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of intermediate 459 and intermediate 460 (1 g) in acetone ( 10 mL) was added a solution of oxone ( 1 .25 g 2.03 mmol) in H20 ( 10 mL ) dropwise under N2 at 0 C. The reaction mixture was stirred at 0 C for 1 hour. Water (20 ml ) was added and the mixture was extracted with EtOAc (3 x 30 ml ). The organic layer was combined, dried over Na2S04, filtered and concentrated. The residue was triturated under EtOAc/ petroleum ether (1/10). The precipitate was filtered off and dried give a mixture of intermediate 220a and intermediate 220b ( 1 50 mg ) as a yellow solid.A mixture of intermediate 457 and intermediate 458 (750 mg), bi.s( pi naco lato )d iboron (942.5 mg, 3.7 mmol ), Pd(dppf)Cl2 (1 13.1 mg, 0. 1 55 mmol ) and KOAc ( 910.6 mg, 9.28 mmol) in THF (20 niL) was stirred at 60C for 2 hours unde N2. Water (30 ml ) was added and extracted with EtOAc (30 niL x 3 ). The organic layers were combined, dried over Na2S04, filtered and concentrated to give a mixture of intermediate 459 and intermediate 460 (1.0 g) as a yellow oil. Step 3 A mixture of intermediate 457 and intermediate 458 (750 mg), bi.s( pi naco lato )d iboron (942.5 mg, 3.7 mmol ), Pd(dppf)Cl2 (1 13.1 mg, 0. 1 55 mmol ) and KOAc ( 910.6 mg, 9.28 mmol) in THF (20 niL) was stirred at 60C for 2 hours unde N2. Water (30 ml ) was added and extracted with EtOAc (30 niL x 3 ). The organic layers were combined, dried over Na2S04, filtered and concentrated to give a mixture of intermediate 459 and intermediate 460 (1.0 g) as a yellow oil. Step 3 3-chloro-5-bromoaniline (1 g, 4.84 mmol) was dissolv ed in 75% I LSO ( 10 mL). Then glycerol (1.1 1 g, 12.1 mmol ) and nitrobenzene (0.59 g. 4.84 mmol ) were added. The reaction mixture was stirred at 150C for 3 hours under N2. EtOAc (50 ml ) was added and the mixture was adjusted to pH to 6-7 with a 30% solution of NaOH in water. The solid was filtered off over celite and the organic layer was separated and ev aporated. The residue was purified by flash column chromatograph over silica gel (gradient eiuent: petroleum ether EtOAc from 20/ 1 to 5/1). The desired fractions were collected and the solvent was evaporated to give a mixture of intermediate 457 and intermediate 458 (750 mg) as a white solid.

The synthetic route of 96558-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WU, Tongfei; BREHMER, Dirk; BEKE, Lijs; BOECKX, An; DIELS, Gaston, Stanislas, Marcella; GILISSEN, Ronaldus, Arnodus, Hendrika, Joseph; LAWSON, Edward, Charles; PANDE, Vineet; PARADE, Marcus, Cornelis, Bernardus, Catharina; SCHEPENS, Wim, Bert, Griet; THURING, Johannes, Wilhelmus, John, F; VIELLEVOYE, Marcel; SUN, Weimei; MEERPOEL, Lieven; (375 pag.)WO2017/32840; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

57946-56-2, 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. 57946-56-2, name is 4-Chloro-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

4-Chloro-2-fluoroaniline (2.9 g, 20 mmol) was dissolved in ethanol (200 mL). Silver sulphate (6.22 g, 20 mmol) was added and then iodine (5.08 g, 20 mmol) was added in small portions. After the addition was complete the reaction mixture was stirred at ambient temperature for 90min. The reaction mixture was filtered through Celite and evaporated to leave a dark oil which was taken up in DCM (200 mL). and washed with 2M sodium hydroxide (2 x 50 mL), saturated sodium thiosulphate (2×50 mL) and water (2×50 mL). The solution was dried (MgSO4) and evaporated to leave the title compound as a dark oil (4.73g, 87%).1H NMR (400 MHz, DMSO-d6) delta 5.30 (2H, s), 7.25 – 7.29 (IH, m), 7.47 (IH, t)

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/82400; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1996-29-8, These common heterocyclic compound, 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, 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.

1-bromo-4-chloro-2-fluorobenzene (5g, 23.9 mmol, 1 eq), 2-methylpiperazine (2.8 g, 1.15 eq), tris – dipalladium (O) (0.43g, 0,05 equiv), rac-BINAP (0.89g, 0.15 eq), sodium tert- butoxide (3.2 g, 1.4 eq) was slurried in toluene (60 mL), followed by the mixture was heated overnight at 65 C.. After cooling to room temperature, it was added ethyl acetate (100mL). The black precipitate was removed by filtration. The filtrate was washed twice with 3N potassium carbonate solution. The organic phase was dried over sodium sulfate, the solid was neutralized with 2N HCl-ether was collected by filtration, washed with ether, and dried in vacuo 1- (4-chloro-2-fluorophenyl) -3- It was obtained methyl piperazine as the dihydrochloride salt.

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 1996-29-8.

Reference:
Patent; CHEMOCENTRYX INCORPORATED; ZHANG, PENGLIE; ZENG, YIBIN; (41 pag.)JP5654467; (2015); B2;,
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. 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., 13526-66-4

mixture of 2.0 g (16.8 mmol) furo[3,2-b]pyridine and anhydrous THF (100 mL) was cooled to -78 C. 10.1 mL (25.2 mmol) of a 1 .6 M solution of n-butyllithium in hexane was added and the resulting mixture stirred for 1 h at -78 C. 6.8 mL (25.2 mmol) of tributyltin chloride was added at -78 C. The cooling bath was removed and the reaction was stirred at room temperature over night. Methanol was carefully added and the solvent evaporated. The obtained residue was purified by flash chromatography to yield 7.4 g of crude product of the corresponding 2-stannylbenzofurane, which was used without further purification. In an inert atmosphere, 3.0 g (12.9 mmol) of 3-bromo-6-chloro-imidazo[1 ,2-b]- pyridazine, 6.85 g (16.8 mmol) of the crude 2-stannylfuro[3,2-b]pyridine, 246 mg (1 .29 mmol) copper (I) iodide and 453 mg (0.645 mmol) bis(triphenylphosphine) palladium(ll)chloride in 100 mL of THF was stirred over night at 85 C in a sealed pressure tube. The solvent was evaporated, the obtained solid was digested in dichloromethane/methanol and filtered off. The solid was washed with methanol and hexane to give 2 g of the title compound as solid material. 1H-NMR (300 MHz, DMSO-de), delta [ppm]= 7.35-7.45 (1 H), 7.57-7.64 (1 H), 7.65-7.70 (1 H), 8.08-8.15 (1 H), 8.40-8.47 (1 H), 8.47-8.52 (1 H), 8.54-8.62 (1 H). LCMS (Method 3): Rt = 0.91 min; MS (ESIpos) m/z = 271 [M+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; BAYER PHARMA AKTIENGESELLSCHAFT; ZORN, Ludwig; EIS, Knut; SCHULZE, Volker; SUeLZLE, Detlev; PUeHLER, Florian; LIENAU, Philip; BOeMER, Ulf; PETERSEN, Kirstin; HAeGEBARTH, Andrea; WO2014/118135; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

126764-17-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 126764-17-8 name is 1-Chloro-6,6-dimethylhept-2-en-4-yne, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

N-Methyl-l-naplithylmethylamine (100 g) was dissolved in water (250 ml). Sodium hydroxide (41.50 g) was dissolved in water (120 ml) and this aqueous sodium hydroxide solution was added to N-Met^yl-I-napththyliriethylatnine solution at 20-400C. The reaction mass was heated to 90-950C and l-chloro-6,6- dimethyl-hept-2-ene-4-yne (96 g, crude viscous oily mass having chromatographic purity by GC 92.40%, as obtained in Step A) was added at 90- 100C. The reaction mass was stirred at 90-1000C for 2 hrs and then cooled to room temperature. Methylene chloride (400 ml) was added and organic layer separated. The methylene chloride extract was washed with water (150 ml). The washed methylene chloride solution was stirred with 300 ml dilute hydrochloric acid at room temperature for 1 h. The methylene chloride layer was washed with water (100 ml) and treated with carbon (4 g) at room temperature. The methylene chloride was stripped to get a residue. The residue was refluxed for 30 min with ethyl acetate (600 ml). The product slurry was cooled to room temperature and stirred for 30 min. Product was filtered and washed with preheated ethyl acetate (160 ml, 40-450C). Product was dried at 55-600C under reduced pressure for 4 h to yield 104 g of Terbinafne hydrochloride, containing 1087 ppm of impurity of Formula IV.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Chloro-6,6-dimethylhept-2-en-4-yne, and friends who are interested can also refer to it.

Reference:
Patent; AUROBINDO PHARMA LTD; WO2007/52089; (2007); 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. 96558-78-0, name is 3-Bromo-5-chlorophenylamine, This compound has unique chemical properties. The synthetic route is as follows., 96558-78-0

To a solution of 3-bromo-5-chloro-aniline (0.2 g, 968.7 pmol, 1 eq), 2-isopropenyl- 4,4,5,5-tetramethyl-l,3,2-dioxaborolane (195.3 mg, 1.2 mmol, 1.2 eq) and K2CO3 (267.8 mg, 1.9 mmol, 2 eq) in 2 mL of dioxane and 0.2 mL of H2O was added Pd(dppf)Ch (70.9 mg, 96.9 pmol, 0.1 eq) and purged with N2 for 3 times. The mixture was stirred at 100C for 12 hours. The reaction mixture was partitioned between 3 mL of water and 5 mL of ethyl acetate. The organic phase was separated, washed twice with 2 mL of brine, dried over Na2SC>4, filtered and concentrated under reduced pressure to give a residue, which was purified by prep-TLC (S1O2, eluting with Petroleum ether : Ethyl acetate = 5: 1) to give 83 mg of compound 2 (495.1 pmol, 51.1 % yield) as a green oil

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; AQUINNAH PHARMACEUTICALS, INC.; VACCA, Joseph, P.; WAGER, Travis, T.; (383 pag.)WO2020/117877; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

363-51-9, 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. 363-51-9, name is 2-Chloro-6-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

Step B: Preparation of l-chloro-3-fluoro-2-isothiocyanatobenzene A solution of 2-chloro-6-fluorobenzenamine (29.2 g, 0.20 mol) in chlorobenzene (200 mL) was treated with N,N-dimethylformamide (0.10 mL) and then thiophosgene (27.6 g, 0.24 mol) dropwise at room temperature. The reaction mixture was heated to reflux for 2.5 hours and allowed to stir at room temperature for 18 hours. The suspension was filtered through a pad of silica gel and washed with hexane. The filtrate was concentrated under vacuum to give a crude oil which was chromatographed on silica gel with hexane to yield the title compound as a light yellow oil (31.5 g). H NMR (CDC13) delta 7.23-7.19 (m, 1H), 7.18-7.13 (td, 1H), 7.10-7.04 (m, 1H).

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; E. I. DU PONT DE NEMOURS AND COMPANY; OBERHOLZER, Matthew, Richard; WO2014/189753; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-70-3, The chemical industry reduces the impact on the environment during synthesis 108-70-3, name is 1,3,5-Trichlorobenzene, I believe this compound will play a more active role in future production and life.

Example 97.2-(4,6-Dichloro- 1 -methyl- 1 H-indazol-3 -yl)-5H-pyrrolo [2,3 -b]pyrazine-7-carboxylic acid [(R)-2- (3-cyano-azetidin-l -yl)-l -methyl-2-oxo-ethyl]-amide 2,4,6-Trichlorobenzaldehyde was prepared according to the procedure outlined in Synthesis 2008, 279. To a solution of 1 ,3,5 -trichlorobenzene (10.0 g, 55.1 mmol) in THF (200 ml) at -78C was slowly added n-BuLi (1.6 M in hexanes, 34.4 ml, 55.1 mmol) over 20 min. The reaction mixture was stirred at -78C for 30 min then DMF (7.5 ml, 96.4 mmol) was added dropwise. The reaction was stirred at -78C for an additional 1.5 h then quenched with 3 N HC1 (200 ml) and warmed to room temperature. The mixture was extracted with EtOAc. The organic layer was washed with sat NaHCC”3 and brine then dried over MgSC^ and concentrated to afford 10.7 g (93%) of 2,4,6-trichlorobenzaldehyde as a white solid.

The chemical industry reduces the impact on the environment during synthesis 1,3,5-Trichlorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Shaoqing; DE VICENTE FIDALGO, Javier; HAMILTON, Matthew Michael; HERMANN, Johannes Cornelius; KENNEDY-SMITH, Joshua; LI, Hongju; LOVEY, Allen John; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; LYNCH, Stephen M.; O’YANG, Counde; PADILLA, Fernando; SCHOENFELD, Ryan Craig; SIDDURI, Achyutharao; SOTH, Michael; WANG, Ce; WOVKULICH, Peter Michael; ZHANG, Xiaohu; WO2013/30138; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

432-21-3, 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 432-21-3 as follows.

1-Chloro-3-iodo-2-trifluoromethyl-benzeneTo a suspension of 3-Chloro-2-trifluoromethyl-phenylamine hydrochloride (30.9 g, iQ 0.16 mol) in H2O (90 mL) was added cone. HCI (65 mL) portion wise allowing the reaction to heat up to -45 0C. The temperature was maintained for 30 min then cooled in an ice bath < 5 0C. CH2CI2 (10 mL) was added and -10 min later a solution of sodium nitrite (13.6 g, 0.197 mol) in H2O (25 mL) was added dropwise. After a further 30 min, a solution of NaI (28.2 g, 0.188 mol) in H2O (50 mL) was again added dropwise keeping the temperature < 5 0C j 5 throughout both additions. After -1 h the reaction was diluted with CH2CI2 (200 mL) and sodium metabisulfite was added until the I2 color had been discharged. The layers were separated and the organic washed with brine, dried and the solvent evaporated to give 1- Chloro-3-iodo-2-trifluoromethyl-benzene (38.3 g, 79%) as an orange solid, which was used without further purification. MS: APCI: M+: 306.0 (305.9) At the same time, in my other blogs, there are other synthetic methods of this type of compound, 432-21-3, and friends who are interested can also refer to it. Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/20306; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

81927-55-1,Some common heterocyclic compound, 81927-55-1, name is Benzyl 2,2,2-trichloroacetimidate, molecular formula is C9H8Cl3NO, 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 alcohol 5 (1.00 g, 8.61 mol) and benzyl 2,2,2-trichloroacetimidate26 (4.34 g, 17.2 mmol, 2.0 equiv) in 1,4-dioxane (15 mL) was added trifluoromethanesulfonic acid (0.15 mL, 1.72 mmol, 0.2 equiv) dropwise at room temperature under nitrogen. The reaction was stirred at room temperature for 1.5 h. The mixture was diluted with dichloromethane (35 mL), washed with saturated aqueous solution of sodium bicarbonate (25 mL*2) and brine (25 mL*3), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel (petroleum ether/ethyl acetate 5:1 to 2:1) to afford the titled compound as colorless oil (1.60 g, 90%). The 1H NMR spectrum was identical to literature data. 1H NMR (400 MHz, CDCl3) delta 7.30-7.19 (m, 5H), 4.62-4.54 (m, 1H), 4.56 (d, J=2.9 Hz, 2H), 3.59 and 3.49 (ABX, JAB=10.8 Hz, JAx=3.3 Hz, JBx=4.3 Hz, 2H), 2.59-2.34 (m, 2H), 2.26-2.13 (m, 1H), 2.09-1.97 (m, 1H).

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

Reference:
Article; Yang, Fan; Feng, Liang; Wang, Nengzhong; Liu, Xuge; Li, Jun; Shen, Yuehai; Tetrahedron; vol. 69; 45; (2013); p. 9463 – 9468;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics