Tag: M.W=200-300

Reference of 468075-00-5,Some common heterocyclic compound, 468075-00-5, name is 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, molecular formula is C7H3BrClF3O, 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) 2-Chloro-5-trifluoromethoxy-benzoic acid methyl ester A mixture of 2-bromo-1-chloro-4-trifluoromethoxy-benzene (5 g, 18.2 mmol), triethylamine (5.51 g, 54.5 mmol), and Pd(dppf)Cl2 (1.33 g, 1.82 mmol) in methanol (200 mL) was stirred at 80 C. under carbon monoxide (50 Psi) overnight, filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography (5% EtOAc in petroleum ether) to give the title intermediate as a colorless liquid (3.4 g, 74% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, its application will become more common.

Reference:
Patent; LONG, Daniel D.; MCKINNELL, Robert Murray; JIANG, Lan; LOO, Mandy; LEPACK, Kassandra; VAN ORDEN, Lori Jean; OGAWA, Gavin; HUANG, Xiaojun; ZHANG, Weijiang; US2013/115194; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 13526-66-4,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.

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

The synthetic route of 13526-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Intellectual Property GmbH; EIS, Knut; PUeHLER, Florian; ZORN, Ludwig; SCHOLZ, Arne; LIENAU, Philip; GNOTH, Mark, Jean; BOeMER, Ulf; GUeNTHER, Judith; HITCHCOCK, Marion; WO2013/34570; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 13918-92-8, The chemical industry reduces the impact on the environment during synthesis 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, I believe this compound will play a more active role in future production and life.

To the solution of 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (400 mg, 1.6 mmol) in pyridine (5 mL) was added 2,4-difluorobenzenesulfonyl chloride (407 mg, 1.9 mmol) slowly, the reaction mixture was stirred at room temperature overnight, the solvent was evaporated in vacuo, and the residue was treated with brine (5 mL) and extracted with EtOAc (3×10 mL). The combined organic layer was evaporated in vacuo, and the residue was purified by column chromatography using petroleum ether_EtOAc=5:1 as eluent to afford the desired product 2,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide as white solid in 59% yield (400 mg). m/z 427 (M+H)+.

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-Difluorobenzene-1-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Su, Weiguo; Zhang, Weihan; Yang, Haibin; US2013/190307; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 33863-76-2, These common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-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.

Example 21Synthesis of {3-Chloro-5-[4-(2,2-dimethyl-propionylamino)-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-phenyl}-acetic acid (Compound 28) cl Step 1: 1-Benzyloxy-3-bromo-5-chloro-benzene; To 1-bromo-3-chloro-5-fluorobenzene (25 g, 112 mmol) and benzyl alcohol (25 mL, 239 mmol) in NMP (200 mL) at room temperature was added sodium hydride (60% in mineral oil; 10.5 g, 263 mmol), and the reaction was heated to 120 C. for 10 hours. The mixture was acidified with 10% aqueous HCl and extracted with EtOAc to give the title compound.

The synthetic route of 33863-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMIRA PHARMACEUTICALS, INC.; US2010/4331; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 16799-05-6 as follows. Product Details of 16799-05-6

The reaction bottle by adding 0.5 millimoles of 2 – phenyl indole, 1.0 mmol 3 – chlorobenzene ethyl alkyne bromine, 3 mmol (6 equiv) potassium hydroxide, 5 muM % (0.025mmol) Pd (OAc)2, 15 muM % (0.075mmol) PCy3, 1.5 ml of N, N – dimethyl formamide, under nitrogen conditions, 130 C stirring for 18 hours, stop heating and stirring, cooled to the room temperature, distilled under reduced pressure to get the crude product, through the column chromatography separation and purification, to obtain the target product, the used column chromatography eluant is petroleum ether, yield 65%. This embodiment of the obtained product hydrogen spectrogram and carbon spectrogram as shown in Figure 11, Figure 12 is shown

According to the analysis of related databases, 16799-05-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; South China University of Technology; Wu Wanqing; An Yanni; Li Jianxiao; Jiang Huanfeng; (16 pag.)CN106866664; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, 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 1996-30-1, SDS of cas: 1996-30-1

A solution of 2-bromo-4-chloro-l-fluorobenzene (2.5 mL, 20 mmol) and sodium thiomethoxide (1.45 g, 20.7 mmol) in DMF (20 mL) was stirred at 100C for 2 h. The reaction mixture was added to water (20 mL) with stirring, and the aqueous mixture was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel(hexanes/EtOAc: 20/1) to afford the title compound. 1H NMR (600 MHz, DMSO-d6): delta 7.74 (d, / = 8.6, 2.3 Hz, 1H), 7.49 (dd, / = 8.6, 2.3 Hz, 1H), 7.28 (d, / = 8.6 Hz, 1H), 2.51 (m, 3H).

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, 3-Bromo-4-fluorochlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; ZHANG, Hongjun; FALCONE, Danielle; TORRES, Luis; BRUBAKER, Jason; ZENG, Hongbo; CAI, Jiaqiang; DU, Xiaoxing; WANG, Chonggang; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146490; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1000572-93-9, name is 1-Bromo-3,4-dichloro-5-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 1000572-93-9, Safety of 1-Bromo-3,4-dichloro-5-fluorobenzene

A mixture of 5-bromo-1,2-dichloro-3-fluorobenzene (2 g, 8.3 mmol), bis(pinacolato)diboron (3.1 g, 12.4 mmol), Pd(dppf)Cl2 (0.33 g, 0.41 mmol), KOAc (2.4 g, 24.7 mmol) in 1,4-dioxane (50 mL) was degassed with N2 for 5 minutes. The reaction mixture was stirred at 70 C. for 16 h. TLC (EtOAc/Petroleum ether=1:5) indicated complete consumption of the bromo starting material. The reaction mixture was poured into water (40 mL) and extracted with EtOAc (3*70 mL). The combined organic phases were dried over anhydrous Na2SO4, and concentrated in vacuo to give a crude residue, which was purified by column chromatography (silica gel, EtOAc/petroleum ether=1:10) to give the boron intermediate (2.0 g, yield: 83.3%) as a white solid.

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; Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; Akama, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen; US2013/131016; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 50638-47-6, 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. 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

B. Ethyl 1-ethyl-7-(3-chloro-4-methoxyphenyl)-6,8-difluoro-1,4-dihydroquinol-4-one 3-carboxylate 300 mg (35.5% yield) was prepared by the method of Example 2 using 1.11 g 4-bromo-2-chloroanisole, 5 ml 2M t-butyl lithium solution, 750 mg zinc chloride and 720 mg ethyl 7-bromo-6,8-difluoro-1-ethyl-1,4-dihydroquinol-4-one 3-carboxylate and 100 mg tetrakis(triphenylphosphine)palladium. A yellow solid of m.p. 280 C. was recovered. NMR (CDCl3, 250 MHz): 8.45 (s, 1H), 8.15 (dd, 1H, J=2 Hz and 9 Hz), 7.55 (s, 1H), 7.4 (m, 1H), 7.1 (d, 1H, J=9 Hz), 4.4 (2q, 4H), 4.0 (s, 3H), 1.55 (t, 3H, J=6.5 Hz), 1.45 (t, 3H, J=6.5 Hz). Anal.: Calcd. for C21H18C1F2NO4.0.5H20: C, 58.00; H, 4.41; N, 3.25%. Found: C, 59.06; H, 4.52; N, 3.17%.

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-chloro-1-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; US4623650; (1986); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 81927-55-1, 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. 81927-55-1 name is Benzyl 2,2,2-trichloroacetimidate, 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.

A stirred solution of (S)- methyl 3-hydroxy-2-methylpropanoate (9.60 g, 81.3 mmol) and benzyl 2,2,2- trichloroacetimidate (22.57 g, 89.4 mmol) in CH2Cl2 (14 mL) was cooled to 0 0C under N2. Triflic acid (0.1 mL) in CH2CI2 (1 mL) was added dropwise. After 10 minutes the reaction became a solid mass. After 1 hour, saturated aqueous NaHCO3 was added and the mixture extracted with Et2O. The organics were dried over MgSO4, filtered and concentrated on a rotary evaporator. Hexane was added and the resulting solids collected by vacuum filtration. The filtrate was concentrated on a rotary evaporator and purified using flash chromatography (5-10% EtOAc/hexane) to give 11.82 g (70%) of (S)-methyl 3-(benzyloxy)-2- methylpropanoate as a colorless oil. Rf= 0.20 (10% EtOAc/hexane). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.08 (d, J=7.14 Hz, 3 H) 2.75 (ddd, J=14.01, 12.64, 7.14 Hz, 1 H) 3.44 – 3.59 (m, 2 H) 3.60 (s, 3 H) 4.46 (s, 2 H) 7.23 – 7.40 (m, 5 H).

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

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2007/84560; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 19752-55-7, A common heterocyclic compound, 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, molecular formula is C6H3BrCl2, 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.

EXAMPLE 3 In the reactor of Example 1, each chlorination of 1-bromo-3,5-dichlorobenzene was chlorinated under the specific condition. The starting materials were respectively preheated at 300 C. and 1-bromo-3,5-dichlorobenzene was fed at a rate of 7.7 g./min. and chlorine was fed at a rate of 550 ml./min. into the reactor. The reaction was continuously carried out at a reaction temperature of 360 C. and a residence time of 14 seconds for 2 hours. The reaction mixture was cooled to collect 1029 g. of the mixture. The reaction mixture was distilled to recover 263 g. of bromine (recovery percent of 84%). The residue contained the object product and a small amount of bromine and it was washed in an aqueous solution of sodium thiosulfate and the product was separated under heating it by a phase separation to obtain 722.5 g. of 1,3,5-trichlorobenzene as the object product (yield of 97.2%).

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; Ishihara Sangyo Kaisha Ltd.; US4368340; (1983); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics