Category: chlorides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 14495-51-3, name is 2-Bromo-5-chlorotoluene, 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 14495-51-3, SDS of cas: 14495-51-3

13.3 ml (0.1 mol) of 2-bromo-5-chlorotoluene was dissolved in 200 ml of anhydrous THF, and 27.7 ml (0.12 mol) of triisopropyl borate was added thereto. After cooling the reaction mixture to-78C over a dry ice-acetone bath, 48 ml (0.12 mol) of 2.5 M n-BuLi (in hexane) was added dropwise thereto for 1 hour, the dry ice-acetone bath was removed, and 150 ml of 3 N HCI was added thereto. The resulting mixture was stirred for 1 hour, and the separated water layer was extracted twice with 100 ml portions of ethyl acetate. The organic layers were combined, washed with a brine solution, dried over anhydrous MgS04, and filtered under a reduced pressure to remove the solvent. The residue was recrystallized from 10% ethyacetate/hexane to obtain 13.8 g (yield 81%) of 4-chloro-2-methylboronic acid as a white solid. ¹H NMR (300 MHz, CDCh) d 8.07 (dd, 1H, J= 5.7 Hz, 2.8 Hz), 7.28-7.26 (m, 2H), 2.76 (s, 3H)

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; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; OSCOTEC INC.; WO2005/123054; (2005); A1;,
Chloride – Wikipedia,
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Related Products of 1127-85-1, 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. 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 2,4-dichloro-5-fluoroquinazoline (22a) (100.00mg, 460.77 mumol, 1.00 eq) in THF (3.00mL) was added methyl (2S,3S)-3-aminobicyclo[2.2.2]octane-2-carboxylate (84.44mg, 460.77 mumol, 1.00 eq) and DIPEA (238.20mg, 1.84mmol, 4.00 eq) at room temperature overnight. H2O (20mL) was added to the mixture and extracted with EtOAc (10mL×3). The combined organic layers were dried over Na2SO4 and concentrated in vacuum. The residue was purified by column chromatography on silica gel with PE:EtOAc (10:1 to 5:1) to give compound 23a (130.00mg, 357.33 mumol, 77.55% yield) as a yellow solid.

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, 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xiong, Jian; Wang, Jingjing; Hu, Guoping; Zhao, Weili; Li, Jianqi; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 249 – 265;,
Chloride – Wikipedia,
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Electric Literature of 7781-10-4, These common heterocyclic compound, 7781-10-4, name is 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, 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 mixture of (S)-tert-butyl 2-amino-4-(((S)-2-fluoro-3-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoate (150 mg, 331 mumol), 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (48 mg, 286) in t-AmOH (3 mL) was added 2.0M t-BuONa in THF (286 muL, 572 mumol) then t-BuXPhos-Pd-G3 (23 mg, 29 mumol) and the resulting mixture was heated to 100 C. for 15 h, cooled to rt, and then concentrated in vacuo to give a tert-butyl (S)-4-(((S)-2-fluoro-3-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino)-2-((7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl) amino) butanoate intermediate, LCMS (ESI+): m/z=584.4 (M+H)+, which was used without further purification. Of the butanoate intermediate, 80 mg, 141 mumol) was taken up in DCM (1 mL) and TFA (400 juL) and the resulting mixture was stirred at rt for 6 h and then concentrated in vacuo. The crude residue was purified by reverse phase prep-HPLC to give the title compound. LCMS (ESI+): m/z=528.3 (M+H)+.

Statistics shows that 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine is playing an increasingly important role. we look forward to future research findings about 7781-10-4.

Reference:
Patent; Pliant Therapeutics, Inc.; CHA, Jacob; DONG, Chengguo; HOM, Timothy; JIANG, Lan; LEFTHERIS, Katerina; LI, Hui; MORGANS, JR., David J.; MUNOZ, Manuel; REILLY, Maureen; ZHENG, Yajun; (232 pag.)US2019/276449; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 39065-95-7,Some common heterocyclic compound, 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, molecular formula is C7H6ClF2NO, 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 stirred solution of 6-hydroxy-5-iodonicotinic acid (40 g) and DMF (3.51 mL) in toluene (315 mL) was treated dropwise with SOd2 (43.9 mL) at RT and then stirred at 85C for 2.5 h. The solvent was evaporated off under reduced pressure and the residue was redissolved in DCM (315 mL). The solution was cooled in an icy water bath and to this solution a mixture of 4-(chlorodifluoromethoxy)aniline (26 .3 g) and Et3N (63 mL) in DCM (315 mL) was added dropwise. The mixture was stirred at rt for 1 hr. Then a saturated aqueous solution of NaHCO3 was added and the mixture was stirred at rt for 10 mm and a solid was formed. The mixture was then diluted with 315 mL of hexane and filtered to collect the white solid, washed with more water and air dried to afford 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-iodonicotinamide (55.97 g). (Rt = 2.28 mi +ESI m/z: MH+ = 459.0).

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

Reference:
Patent; ASTAR BIOTECH LLC; LI, Lianhai; YU, Chunrong; HUANG, Haihong; (94 pag.)WO2017/186148; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 13078-80-3,Some common heterocyclic compound, 13078-80-3, name is 2-(2-Chlorophenyl)ethanamine, molecular formula is C8H10ClN, 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 1 Into a 100 ml reaction flask equipped with a condenser, a thermometer and a stirrer, 15.56 g (0.1 mol) of 2-chlorophenethylamine, 22.0 g (0.11 mol) of a 20% sodium hydroxide aqueous solution and 0.176 g (0.5 mol %) of quinoline copper were charged, and reacted at 110 C. for 8 hours. The reaction mixture thereby obtained was subjected to liquid separation to separate the aqueous layer from the organic layer. The organic layer was washed with an acid and distilled to obtain 11.4 g of indoline (boiling point: 94-95 C./11 mmHg). The purity was 99.5%, and the yield was 96%.

The synthetic route of 13078-80-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ihara Chemical Industry Co., Ltd.; US4673749; (1987); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 694-80-4, 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. 694-80-4 name is 1-Bromo-2-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.

General procedure: To a round bottle with a magnetic stir bar, ligand (0.01% mmol), PdCl2 (0.01% mmol), aryl halides (1.0 mmol), phenylboronic acid (1.2 mmol), K2CO3 (2.0 mmol) and 6 ml of solvent were added. The reaction mixture was conducted at room temperature for the required time, and then the solvent was removed under reduced pressure. The residual was diluted with Et2O (5 mL), followed by extraction twice (2×5 mL) with Et2O. The organic layer was dried with anhydrous MgSO4, filtered and evaporated under vacuum. The conversions rates were analyzed by gas chromatography, based on the peak area normalization method. The corrected factor was determined by samples against a standard of n-heptane. The crude products were purified by silica-gel column chromatography using petroleum ether-ethyl acetate (20:1) as an eluent, and the isolated yield was then calculated based on the feeding of the aryl halide. The isolated corresponding products were characterized by 1H NMR and 13C NMR.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-chlorobenzene, and friends who are interested can also refer to it.

Reference:
Article; Zhou, Zhen; Cao, Gao; Liu, Ning; Chemistry Letters; vol. 48; 6; (2019); p. 547 – 550;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 108047-39-8, These common heterocyclic compound, 108047-39-8, name is 2-(Aminomethyl)-4-chloroaniline, 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 solution of the amine of preparation 10 (6. 4 g, 41 MMOL) in tetrahydrofuran (50 ML) was added to a solution of the oxadiazole of preparation 5 (4.56 g, 16 MMOL) in tetrahydrofuran (50 ML) and the mixture was heated to 50 C for 18 hours. The reaction mixture was evaporated under reduced pressure and the residue was purified by chromatography on silica gel using methanol in DICHLOROMETHANE as eluant (5: 95), to give the title compound as a white solid (4.65 g). APCI MS M/Z 399 [MH] + ‘H NMR (400MHZ, CDCI3) : 8 1.95 (m, 2H), 2.20 (m, 2H), 3.10 (m, 2H), 3.20 (m, 1H), 3.80 (s, 2H), 4.00 (s, 2H), 4.30 (m, 2H), 6.60 (m, 1H), 6.65 (t, 1H), 6.70 (d, 1H), 7.00 (s, 1H), 7.05 (d, 1H), 7.50 (t, 1H), 8.20 (d, 1H)

The synthetic route of 108047-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/74291; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1435-48-9, name is 2,4-Dichloro-1-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 1435-48-9, HPLC of Formula: C6H3Cl2F

[209] Alternate preparation: To a solution of 2,4-dichloro-1-fluorobenzene (100 g, 0.606 mol) in THF (1.4 L) under nitrogen at -78 C, was added a 2.5 M solution of n-BuLi in hexanes (267 ml_, 0.666 mol) dropwise over a period of 30 min, maintaining the temperature between -70 to -78 C. After 1.5 h stirring at -78 C, methyl formate (72.6 ml_, 1.21 mol) was added slowly, and the reaction mixture was stirred overnight, warming up to rt. The reaction was quenched with sat. aqueous NH4CI (200 ml.) and the organic layer was separated. The organic solvents were removed by distillation at atmosphere pressure and the crude material which contained a small amount of THF was crystallized from hexanes to give the title compound.

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; OSI PHARMACEUTICALS, INC.; CHEN, Xin; JIN, Meizhong; KLEINBERG, Andrew; LI, An-hu; MULVIHILL, Mark, J.; STEINIG, Arno, G.; WANG, Jing; WO2010/59771; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 3460-24-0, These common heterocyclic compound, 3460-24-0, name is 1,4-Dibromo-2-chlorobenzene, 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.

1,4-Dibromo-2-Chloro-Benzene 1eq(45.8 g), 2-aminophenylboronic acid 2eq (46.5 g), Pd (PPh3) 4 5 mol% (9.8 g) and K2CO3 2eq (46.9 g) were dissolved in toluene 1-fold, 550 ml) and distilled water (5 times as much as K2CO3, 235 ml), and the mixture was stirred under reflux for 18 hours under a nitrogen stream. After completion of the reaction, the reaction mixture was extracted with toluene and distilled water. The organic layer was dried with magnesium sulfate (MgSO4) and filtered, and the filtrate was concentrated under reduced pressure. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), and the resulting solid was recrystallized from dichloromethane and acetone to obtain intermediate d-1 (23.5 g, Y = 47%).

The synthetic route of 3460-24-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI Co., Ltd; Jang Gi-po; Kim Jun-seok; Lee Seung-jae; Hong Jin-seok; Kim Chang-u; Jeong Seong-hyeon; Kim Yeong-gwon; Ryu Eun-seon; Jeong Ho-guk; (30 pag.)KR2017/111538; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1205-71-6, name is 4-Chloro-N-phenylaniline, 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 1205-71-6, Recommanded Product: 1205-71-6

General procedure: To a 50 mL of two-neck round-bottomed flask charged with a magnetic stirrer bar, were successively added 1-Bromo(2-diphenylphosphoryl)ethyne (1) (305 mg, 1.0 mmol), diphenylamine(203 mg, 1.2 mmol, 1.2 equiv), K3PO4 (637 mg, 3.0 mmol, 3.0 equiv) and dehydrated toluene (5mL). After the mixture was stirred at 80 C for 15 h, the reaction mixture was quenched with 1 mL of saturated NH4Cl aq., and extracted with ethyl acetate and H2O, and dried over brine and MgSO4. The crude product was purified by flash chromatography (hexane/EtOAc, 1:2) to afford the corresponding phosphoryl ynamine 2a (240 mg) in 61% yield.

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:
Article; Okuda, Yasuhiro; Seo, Tomoyo; Shigezane, Yuki; Watanabe, Hikaru; Akashi, Haruo; Iwanaga, Tetsuo; Orita, Akihiro; Chemistry Letters; vol. 48; 12; (2019); p. 1484 – 1487;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics