Month: September 2021

Synthetic Route of 38762-41-3, The chemical industry reduces the impact on the environment during synthesis 38762-41-3, name is 4-Bromo-2-chloroaniline, I believe this compound will play a more active role in future production and life.

Description 13; (4-Bromo-2-chlorophenyl)-(tetrahydropyran-4-yl)-amine (D13); A mixture of 4-bromo-2-chloro-phenylamine (0.5 g, 2.422 mmol), tetrahydropyran-4- one (1.308 ml, 10.898 mmol), and sodium triacetoxyborohydride (2.31 g, 10.898 mmol) in DCE (20 ml) was stirred at room temperature for 16 h. The reaction mixture was washed with NaHCO3 (aqueous sat. solution), dried (Na2SO4) and the solvent was evaporated in vacuo. The residue was purified by column chromatography (silica gel; heptane/DCM up to 40% as eluent). The desired fractions were collected and evaporated in vacuo to yield compound D13 (0.383 g, 52%) as white solid. LCMS: MW (theor): 289; [MH+]: 290; RT (min): 4.39 (Method 1).

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-2-chloroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC.; ADDEX PHARMA S.A.; CID-NUNEZ, Jose, Maria; TRABANCO-SUAREZ, Andres, Avelino; MACDONALD, Gregor, James; WO2010/60589; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 328-72-3, 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. 328-72-3 name is 3,5-Bis(trifluoromethyl)chlorobenzene, 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.

STR7 Preparation of 3,5-bis-(trifluoromethyl)-benzonitrile By the method of Example 3, 124 g of 1-chloro-3,5-bis-(trifluoromethyl)-benzene in 120 ml of ethyl methyl ketone gave 61.4 g (51.2% of theory) of 3,5-bis-(trifluoromethyl)-benzonitrile (b.p.45 mbar: 88 C.). After 20 hours, the conversion was approximately 60%. 4.5% of coupling products had formed.

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

Reference:
Patent; Bayer Aktiengesellschaft; US6162942; (2000); A;,
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. 348-59-4, name is 2,5-Dichlorofluorobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 348-59-4

[ETHYL 4-[(4-HYDROXY-1-PIPERIDINYL)METHYL]-?-PHENYL-1-PIPERIDINEACETATE ] (0.135 g) was dissolved in NMP (3 mL). 1, 4-Dichloro-2-fluorobenzene (0.2 mL) and potassium t- butoxide (56 mg) were added and the solution was heated to [50 C] for 40 h. The solution was cooled to ambient temperature and few drops of aqueous sodium hydroxide solution were added. The mixture was stirred for 60 h, then acetic acid (few drops) was added and the solvent was distilled. The residue was purified by HPLC (0.2% aqueous ammonia: acetonitrile; gradient 95: 5 to 50: 50) to give the title compound (21 mg). MS [[M+H] +] (ES+) 477/479 [IH] NMR [8 (CD30D)] 1.45 (1H, q), 1.68-1. 96 (9H, m), 2.16-2. 21 (2H, m), 2.25-2. 34 (2H, m), 2.57-2. 65 (3H, m), 2.80-2. 93 (2H, m), 4.29-4. 36 [(1H,] m), 4.38-4. 44 [(1H,] m), 6.83 [(1H,] dd), 7.02 (1H, d), 7.23 (1H, d), 7.32-7. 36 (3H, m), 7.44-7. 49 (2H, m)

The synthetic route of 348-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2004/29041; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 61881-19-4, These common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, 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.

General procedure: In a typical experimental procedure, a dry, two-necked, 50 mL round-bottomed flask equipped with a nitrogen inlet was charged with 5 mL of dry MeCN, 0.117 g (1.0 mmol) of indole and 0.24 g (1.0 mmol) of NaH. The solution was stirred under a nitrogen atmosphere at room temperature for 30 min, then a solution of 2a (1.0 mmol in 2 mL of dry MeCN) was added dropwise via a syringe. The mixture was stirred at room temperature for 20 h under an N2 atmosphere and then filtered. After removing the solvent under reduced pressure, the crude product was purified by preparative thin-layer chromatography on silica gel [eluent: n-hexane/EtOAC, 4:1] to give the product 4a. The products obtained from indole-3-carbaldehyde were purified by recrystallization from EtOH (twice).

Statistics shows that 2,2,2-Trifluoro-N-phenylacetimidoyl chloride is playing an increasingly important role. we look forward to future research findings about 61881-19-4.

Reference:
Article; Darehkordi, Ali; Rahmani, Fariba; Hashemi, Vahide; Tetrahedron Letters; vol. 54; 35; (2013); p. 4689 – 4692;,
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.

Intermediate 14Preparation of N- [5 -bromo-2-(methyloxy)- 3 -pyridinyll -2,4-difluorobenzenesulfonamideTo a cooled (0 0C) solution of 5-bromo-2-(methyloxy)-3-pyridinamine (20.3 g, 100 mmol) in Pyridine (200 rnL) was added slowly 2,4-difluorobenzenesulfonyl chloride (21.3 g, 100 mmol) over 15 min (reaction became heterogeneous). The ice bath was removed and the reaction was stirred at ambient temperature for 16 h, at which time the reaction was diluted with water (500 mL) and the solids filtered off and washed with copious amounts of water. The precipitate was dried in a vacuum oven at 50 0C to give N-[5-bromo-2- (methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide (12 g, 31.6 mmol, 31.7 % yield). MS (ES) m/e 380.9, 379.0 (M + H)+.

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:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157191; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 18282-59-2, name is 4-Bromo-1,2-dichlorobenzene, 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. Formula: C6H3BrCl2

Mg (1.93 g, 79.4 mmol) was suspended in Et2O (50 ml). A chip of I2 was added, then heated to 45° C. 3,4-dichlorobenzylchloride (5.50 ml, 39.7 mmol) in Et2O (50 ml) was added slowly and the mixture was stirred at 45° C. for 2 h, then cooled to 23° C. In a second flask, CuCN (71 mg, 0.79 mmol) was suspended in Et2O (20 ml), then cooled to -30° C. under N2. The Grignard reagent was cannulated into the second flask, then warmed to -15° C. Compound 70 (4.75 g, 7.94 mmol) in Et2O (50 mL) was added dropwise. The mixture was stirred at -15° C. overnight, then warmed to 23° C. and stirred for 24 h. The reaction was quenched with 25percent aqueous sodium citrate at 0° C. and the product extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. Purification by silica gel chromatography (eluant: 3percent to 6percent EtOAc:hexane) gave 3.73 g (4.9 mmol, 62percent) of the product 71. MS (M+1): 759.

The synthetic route of 4-Bromo-1,2-dichlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; US2005/182095; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 367-22-6,Some common heterocyclic compound, 367-22-6, name is 4-Chloro-3-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.

To a suspension of 4-chloro-3-fluoroaniline (10.67 g, 73.3 mmol) and Na2CO3 (24.5 g, 125 mmol) in Et20 (300 ml) at -10 C under N2 was added TFAA (12.23 ml, 88 mmol) dropwise. The mixture was allowed to warm to rt for 18 h. The reaction mixturewas diluted with hexane (300 ml), and filtered. The filtrate was washed with ice-water,10% aq NaHCO3, and brine, dried over Na2SO4, and concentrated. A pale yellow solid obtained as N-(4-chloro-3-fluorophenyl)-2,2,2-trifluoroacetamide (17 g, 96 % yield). MS (ESI) m/z: 242.1 (M+H)t

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-3-fluoroaniline, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMITH II, Leon M.; PINTO, Donald J. P.; CORTE, James R.; EWING, William R.; (163 pag.)WO2016/205482; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 95-81-8, 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. 95-81-8, name is 2-Chloro-5-methylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Reference Example 6 4-(4-Hydroxyanilino)-6-(2-chloro-5-methylanilino)pyrimidine The title compound was prepared in a similar manner to that of Reference Example 4 from 4-(4-hydroxyanilino)-6-chloropyrimidine (Reference Example 5) by reaction with 2-chloro-5-methylaniline in butan-1-ol in the presence of catalytic concentrated hydrochloric acid. The mixture was heated at reflux for 18 hours, concentrated and the residue purified by column chromatography eluding with DCMN:MeOH: concentrated ammonia (94:5:1). Yield 84%. NMR: 2.26 (3H, s), 5.85 (1H, s), 6.68 (2H, d), 6.93 (1H, d), 7.19 (2H, d), 7.32 (1H, d), 7.46 (1H, s), 8.09 (1H, s), 8.44 (1H, s), 8.69 (1H, s), 9.11 (1H, s); m/z 327 (MH+).

The synthetic route of 2-Chloro-5-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; US6632820; (2003); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 468075-00-5, name is 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, 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. Safety of 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene

Into a two-dram vial was added-2-bromo-1-chloro-4-(trifluoromethoxy)benzene (100 mg, 0.363 mmol), the title compounds from Example 3 Step B (100 mg), and SPhos biaryi precatalysis (26.2 mg, 0.036 mmol), cesium carbonate (237 mg. 0.726 mmol) followed by 1,4-dioxane (2 ml). The mixture was degassed by N2 for 5 mm, then heated at 100C for 24 h. Concentrate to remove solvents. The afforded crude was purified with normal phase silica gel chromatography (0 to 100% EtOAc in 1:1 mixed hexanes/DCM) to give desired product (as a mixture of 2).

The synthetic route of 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHELLIAH, Mariappan; CHU, Hong Dong; COX, Jason, M.; DEBENHAM, John, S; EAGEN, Keith; LAN, Ping; LONDON, Clare; PLOTKIN, Michael, A.; SHAH, Unmesh; SINZ, Christopher Joseph; SUN, Zhongxiang; VACCARO, Henry, M.; VENKATRAMAN, Skikanth; WO2014/59232; (2014); A2;,
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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 69411-05-8

Intermediate B (200 mg, 0.41 mmol), 3-chloro-5-(trifluoromethyl)benzenamine (80 mg, 0.41 mmol) and DIEA (106 mg, 2 mmol) were dissolved in THF (20 ml_). The reaction mixture was heated to 85C for 18 hours. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel (eluent DCM:methanol 100. to 98:2) to followed by pre-HPLC to give the titled compound (14 mg, 5.8%) as a white solid. LCMS (method B): 2.66 min [MH]+=592.2. 1H NMR (400 MHz, DMSO-d6) delta ppm 3.45 (s, 3 H) 5.81(d, J= 6.4 Hz, 1 H) 7.30 (m, 4 H) 7.43 (m, 3 H) 7.61 (d, J=8.8, 2 H) 7.90 (m, 4 H) 8.55 (s, 1 H) 9.18 (s, 1 H) 9.39 (s, 1 H) 9.57 (s, 1 H).

The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CATALYST THERAPEUTICS PTY LTD; LESSENE, Guillaume Laurent; GARNIER, Jean-Marc; CUZZUPE, Anthony Nicholas; FEUTRILL, John Thomas; CZABOTAR, Peter Edward; SHARMA, Pooja; (142 pag.)WO2016/127213; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics