Tag: M.W=200-300

These common heterocyclic compound, 1008361-80-5, name is 4-Bromo-3-chlorobenzene-1,2-diamine, 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. Application In Synthesis of 4-Bromo-3-chlorobenzene-1,2-diamine

To a solution of 4-bromo-3-chlorobenzene-l,2-diamine (0.15 g) and triethylamine (285 mu.) in DMF (2 mL), 90 mu. of ethyl 2-bromoacetate was added and the reaction mixture was heated at 80 C overnight. After this time, most of the volatiles were removed under reduced pressure and the residue was purified by column chromatography (silica gel, 0-2 % MeOH in DCM) to afford the title compound as a brown solid.

The synthetic route of 4-Bromo-3-chlorobenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (447 pag.)WO2017/35408; (2017); A1;,
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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. 38762-41-3, name is 4-Bromo-2-chloroaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Bromo-2-chloroaniline

Preparation 94 2-Chloro-4-(oxazol-5-yl)aniline Palladium acetate (5.4 mg, 0.024 mmol) was added to a solution of 4-bromo-2-chloroaniline (0.1 g, 0.484 mmol), oxazole (0.064 mL, 0.969 mmol), di(1-adamantyl)-n-butylphosphine (0.017 g, 0.048 mmol), pivalic acid (0.020 g, 0.194 mmol) and potassium carbonate (0.201 g, 1.453 mmol) in DMA (2.4 mL). The reaction mixture was heated at 110 C. overnight before being diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with (Cyclohexane/EtOAc 80/20 to 60/40) to give the title product as a white solid (35 mg, 37%). 1H NMR (500 MHz, CDCl3): delta 4.25 (br s, 2H), 6.82 (d, J=8.3 Hz, 1H), 7.20 (s, 1H), 7.38 (dd, J=8.3, 2.0 Hz, 1H), 7.58 (d, J=2.0 Hz, 1H), 7.87 (s, 1H). LC (Method B)-MS (ESI, m/z) tR 2.47 min, 195 [(M+H+), 100%].

The synthetic route of 38762-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; Bavetsias, Vassilios; Atrash, Butrus; Naud, Sebastien Gaston Andre; Sheldrake, Peter William; Blagg, Julian; US2013/345181; (2013); A1;,
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These common heterocyclic compound, 102170-53-6, name is 4-Bromo-5-chloro-2-methoxyaniline, 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. Product Details of 102170-53-6

A 500-mL round-bottom flask was charged with (E)-/er/-butyl 3-(3-methoxy-3-oxoprop-l-en-l-yl)-4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-l(2H)-carboxylate (Preparation 3a, (10.8 g, 26.0 mmol), xantphos (1.88 g, 3.25 mmol), cesium carbonate (25.4 g, 78.0 mmol), 4-bromo-5-chloro-2-methoxyaniline (6.15 g, 26.0 mmol), tris(dibenzylideneacetone)dipalladium (0) (1.19 g, 1.30 mmol) and 1,4-dioxane (130 mL) then sparged with nitrogen for 15 min. The reaction mixture stirred vigorously for 20 h at ambient temperature. The reaction mixture was subsequently vacuum filtered through a 1.0 cm plug of silica gel and the pad was rinsed with EtOAc (3 x 150 mL). The filtrate was concentrated under reduced pressure to give a brown foam that was used immediately without further purification.[00562] The product was diluted with MeOH (260 mL) and transferred to a 350-mLpressure vessel equipped with a stir bar. The reaction vessel was subsequently charged with sodium methoxide (25 wt. % in MeOH, 2.97 ml, 13.00 mmol) and sealed with a Teflon cap equipped with a pressure-relief valve. The reaction vessel was placed in a 70 C oil bath and stirred vigorously. After 5 h, the reaction mixture was allowed to cool to ambient temperature, transferred to a 1-L round-bottom flask with additional MeOH and concentrated under reduced pressure. The brown oil was redissolved in DCM (150 mL) and filtered through a pad of Celite (3 cm) to facilitate loading the material onto a column. The Celite pad was rinsed with DCM (3 x 50 mL). The brown filtrate was concentrated under reduced pressure and purified by flash column chromatography (340-g Biotage column, eluent: gradient, 5 to 35% 3:1 EtOAc/EtOH in heptane with DCM as a 10% additive) to afford (Rac)-tert-butyl 1-(4-bromo-5-chloro-2-methoxyphenyl)-2-oxo-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate (9.12 g, 19.4 mmol, 74.7 % yield) as a tan solid.

The synthetic route of 4-Bromo-5-chloro-2-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
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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, Recommanded Product: 2-Bromo-5-chlorotoluene

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,
Chlorides – an overview | ScienceDirect Topics

Reference 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;,
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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.

Reference Example-10 A solution of 1-bromo-4-chloro-2-fluoro benzene (10.0 g, 47.8 mmol) in THF was added dropwise to a suspension of magnesium (1.28 g, 52.5 mmol) in THF (50 mL) at 40 C. (oil bath temperature) in the presence of a catalytic amount of iodine in an argon gas atmosphere, whereby a Grignard reagent was prepared. The Grignard reagent was added dropwise to a solution of diethyl oxalate (8.37 g, 57.3 mmol) in THF at -50 C., and the temperature was slowly raised to room temperature, followed by stirring for 18 hours. After the reaction was completed, the reaction solution was poured into ice, then, acidified with concentrated hydrochloric acid, and the resultant product was extracted with ether (100 mL*2, 50 mL*1). The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure, whereby an orange oily crude product (12.9 g) was obtained. This was purified by silica gel column chromatography (hexane:ethyl acetate=10:1), whereby ethyl 2-(4-chloro-2-fluorophenyl)-2-oxoacetate (4.17 g, yield: 41%) was obtained as a yellow oily material. 1H-NMR (400 MHz, CDCl3): delta1.40 (t, J=7.1 Hz, 3H), 4.43 (q, J=7.1 Hz, 2H), 7.22 (dd, J=1.8 and 10.2 Hz, 1H), 7.31 (dd, J=1.8 and 8.4 Hz, 1H), 7.89 (dd, J=7.6 and 8.4 Hz, 1H). 19F-NMR (376 MHz, CDCl3): delta-109 (s, 1F).

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; KAKEN PHARMACEUTICAL CO., LTD.; SAGAMI CHEMICAL RESEARCH INSTITUTE; KOBAYASHI, Osamu; NIIKURA, Naoko; INOUE, Tomoko; MIZUTA, Satoshi; TAKATSUNA, Reiko; HIRAI, Kenji; SHIROUZU, Kentaro; OBATA, Miyoo; (183 pag.)US2016/24110; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 60811-18-9,Some common heterocyclic compound, 60811-18-9, name is 4-Bromo-1-chloro-2-fluorobenzene, molecular formula is C6H3BrClF, 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. 4-chloro-3-fluorobenzoylpropionic acid To a solution of succinic anhydride (6.0 g) in tetrahydrofuran (60 ml) was added dropwise the Grignard prepared from 1.5 g (0.062 mole) of magnesium turnings and 10.5 g (0.05 mole) of 1-bromo-4-chloro-3-fluorobenzene using the procedure of part a. When the addition was completed, the resulting suspension was stirred for 2 hours at 45 C. after which water (100 ml) was added slowly and the resulting mixture was acidified with concentrated hydrochloric acid to pH=1. The ether layer was separated and extracted with 5% aqueous sodium hydroxide (3*100 ml). The combined aqueous solutions were washed with ether (1*100 ml). The combined basic aqueous layers were acidified with concentrated hydrochloric acid to pH 1 and extracted with ethyl acetate (3*150 ml). The combined organic extracts were washed with water (1*150 ml) and brine (1*150 ml), dried over anhydrous magnesium sulfate and evaporated in vacuo to give 7.1 g (62%) of the product as a yellow orange solid. The resulting acid was converted to the desired product using the procedure of Example 11d-e. Compound 83 was prepared following essentially the same procedure.

The synthetic route of 60811-18-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Company; US5552409; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 93765-83-4, 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. 93765-83-4, name is 1-Bromo-5-chloro-2-fluoro-4-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 12To a solution of 1-bromo-5-chloro-2-fluoro-4-methylbenzene (Comm, 10 g, 44.7 mmol) in methanol (200 ml_) was added 1 ,1′-binaphthalene-2,2′-diylbis(diphenylphosphine) – dichloropalladium (1:1) (358 mg, 0.447 mmol) and N,N-diethylethanamine (8.11 ml_, 58.2 mmol). The resulting mixture was placed in a bomb and pressurized with carbon monoxide to 80 psi and heated at 80C for 18 hours. The reaction mixture was then concentrated in vacuo to yield a semi-solid, which was dissolved in EtOAc (300 ml_) and washed with water (200 mL). The organic layer was separated, dried over magnesium sulphate, filtered and concentrated in vacuo to yield an orange oil, which solidified on standing (9.87 g). The solid was purified by silica gel chromatography eluting with 0 to 20% EtOAc in heptane to afford the title compound as a crystalline white solid (8.47 g, 93%).1H NMR (400 MHz, CDCI3): delta 2.40 (s, 3H), 3.92 (s, 3H), 7.03 (d, 1 H), 7.91 (d, 1 H) LCMS Rt = 1 .64 minutes Molecular ion not observed

The synthetic route of 1-Bromo-5-chloro-2-fluoro-4-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; BROWN, Alan, Daniel; RAWSON, David, James; STORER, Robert, Ian; SWAIN, Nigel, Alan; WO2012/7868; (2012); A2;,
Chloride – Wikipedia,
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A common compound: 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 54932-72-8

Nitrogen gas was purged through a stirred solution of 5-bromo-2-chiorotoluene (452 muIota, 3.41 mmol) in 1 ,4-dioxane (15 ml) for 30 mins. 2,2′-Bis(diphenylphosphino)-1 , 1 ‘- binaphthyl (212 mg, 0.34 mmol), Pd(OAc)2 (153 mg, 0.68 mmol) and Cs2C03 (2.22 g, 6.81 mmol) were then added. The stirred solution was then purged of nitrogen for a further 30 min after which 1-Boc-3-aminopyrrolidine (745 muIota, 4.09 mmol) was added and solution stirred at reflux for 48 h under N2. The solvent was then evaporated in vacuo and the crude residue dissolved in EtOAc (40 ml) which was then washed with water (2 x 30 ml), brine (2 chi 30 ml), dried with Na2S04, filtered and concentrated. The crude residue was then purified by column chromatography (100% CyHex to 10% EtOAc/CyHex) to obtain WIN-321 -142-01 as a solid (111 mg, 10.4%).1H NMR (CDCI3): delta 7.13 (d, J 8.4 Hz, 1H), 6.48 (d, J 2.6 Hz, 1H), 6.39 (dd, J 8.58, 2.86 Hz, 1H), 3.99 (br. s., 1H), 3.79-3.57 (m, 2H), 3.56-3.38 (m, 2H), 3.31 -3.14 (m, 1H), 2.30 (s, 3H), 2.10 – 2.26 (m, 1 H), 1.96 – 1.79 (m, 1 H), 1.47 (s, 9H). MS, m/z = 255 (100) [M-56], 257 (30).

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, 54932-72-8, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNIVERSITY OF MELBOURNE; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; SLEEBS, Brad; PURCELL, Damian Francis John; JACOBSON, Jonathan; LEWIN, Sharon; NGUYEN, William; (163 pag.)WO2017/219083; (2017); A1;,
Chloride – Wikipedia,
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Application of 13918-92-8, 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. 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4.00 g (21.4 mmol) C-3, 4.3 mL (32 mmol) 2,4-difluorobenzenesulfonyl chloride, 5.2 mL (64 mmol) pyridine and 50 mL DCM is stirred at RT for 5 h. After completion of the reaction, the solvent is removed under reduced pressure, the crude product is taken up in 50 mL water and extracted twice with 100 mL DCM. The combined organic layers are dried over MgSO4 and the solvent is removed under reduced pressure. The crude product can be used without further purification. Yield: 7.88 g (91%).

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; The designation of the inventor has not yet been filed; EP2546249; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics