Chlorides-buliding-blocks

A common heterocyclic compound, 108-41-8, name is 1-Chloro-3-methylbenzene, molecular formula is C7H7Cl, 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. 108-41-8.

General procedure: Under an N2 atmosphere, KOtBu (1.3 mmol), complex 1 (1 mol %), dioxane (2 ml), amines (1.3 mmol) and aryl chlorides (1.0 mmol) were successively added into a Schlenk tube. The mixture was stirred vigorously at 90 C for 4 h. Then the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: PE/EA = 15:1) to give the pure products. The reported yields are the average of two runs.

The synthetic route of 1-Chloro-3-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nirmala, Muthukumaran; Saranya, Gandhi; Viswanathamurthi, Periasamy; Bertani, Roberta; Sgarbossa, Paolo; Malecki, Jan Grzegorz; Journal of Organometallic Chemistry; vol. 831; (2017); p. 1 – 10;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6940-78-9, 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. 6940-78-9 name is 1-Bromo-4-chlorobutane, 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.

1-bromo-4-chlorobutane (3.4 g, 20 mmol), anhydrous potassium carbonate powder (4.14 g, 30 mmol) and 7-hydroxy-3,4-dihydro-2(1H)quinolinone 10 mmol)Was added to 10 ml of acetone, refluxed for 24 hours,, the reaction solution was evaporated to dryness, and the mixture was partitioned with 20 ml portions of dichloromethane and water. The organic layer was extracted with 20 ml of water * 2 and 20 ml of saturated brine successively, dried over anhydrous magnesium sulfate , Evaporate to dryness to give a pale yellow powder. The obtained powder is washed with slurry with 20 ml * 3 of n-hexane, filtered, and dried to obtain 1.98 g of 7-(4-chlorobutoxy)-3,4-dihydro-2(1H)quinolinone. Yield is 78%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-chlorobutane, and friends who are interested can also refer to it.

Reference:
Patent; JIANGSU HENGYI PHARMACEUTICAL COMPANY LIMITED; SHANGHAI INSTITUTE OF PHARMACEUTICAL INDUSTRY; Li, JIANQI; PENG, SHAOPING; CAI, WANGPING; GAO, KAI; (39 pag.)JP5714152; (2015); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, molecular formula is C6H3BrClF, 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. 1996-30-1.

[0136] A solution of 2-bromo-4-chloro-1-fluorobenzene (175 muL, 1.377 mmol) in THF (4.59 mL) at 78 C. was treated with n-BuLi (2.6 M, 741 muL, 1.928 mmol) and the reaction mixture was stirred for 30 min. To this was added tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (250 mg, 0.918 mmol) in one portion. The cooling bath was removed and the resulting reaction mixture was allowed to warm to rt and stirred for 1.5 h. Purification by automated flash silica gel chromatography using 10% EtOAc in hexanes afforded tert-butyl 4-(5-chloro-2-fluorobenzoyl)piperidine-1-carboxylate (287.9 mg, 92%) as a yellow oil. ESI-MS m/z [M+Na]+ 364.20

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Brown, Jason; Hitchcock, Steve; Hopkins, Maria; Kikuchi, Shota; Monenschein, Holger; Reichard, Holly; Schleicher, Kristin; Sun, Huikai; Macklin, Todd; US2015/175602; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6940-78-9, Adding some certain compound to certain chemical reactions, such as: 6940-78-9, name is 1-Bromo-4-chlorobutane, 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 6940-78-9.

General procedure: General procedure for the preparation of omega-naphthyloxyhalo alkanes (3a-c) involves refluxing of mixture of beta-naphthol (1) (20 g, 0.14 mol), anhydrous K2CO3 (100 g, in excess) and bromochloroalkane 2 (0.14 mol) in dry acetone (200 mL) for12-15 h. Reaction mixture was filtered and filtrate was concentrated to get oily compound, which was crystallized with benzene-hexane to give the colourless crystals of pure desired compound (Scheme-I) [48].

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 6940-78-9.

Reference:
Article; Zaidi, Sadaf; Chaturvedi, Devdutt; Saxena, Mridula; Srivastava, Richa; Asian Journal of Chemistry; vol. 31; 10; (2019); p. 2201 – 2210;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

933190-51-3, A common compound: 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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.

General procedure: To a solution of 6a-6c (1 mmol) in THF (5 mL) was addedmorpholine (or (S)-3-methylmorpholine, or 8-oxa-3-azabicyclo[3.2.1]octane) (1.2 mmol) and Et3N (2.2 mmol). The mixture washeated under reflux for 12 h. The crude product was extracted with CH2Cl2, dried over Na2SO4, purified over silica gel chromatographyeluting with PE and EtOAc to give 7a-7g [43].

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, 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mao, Beibei; Gao, Shanyun; Weng, Yiran; Zhang, Liangren; Zhang, Lihe; European Journal of Medicinal Chemistry; vol. 129; (2017); p. 135 – 150;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13726-14-2, name is 4-Chloro-3-methoxyaniline, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 13726-14-2

5-Nitro-2-chloro aniline (50.0 g, 0.289 mol) in 30 % sulfuric acid (300 ml) was stirred at RT for 2 h. Sodium nitrite (21.0 g, 0.304 mol) in water (50 ml) was added slowly at 0C. After 15 mins, this solution was added slowly to dilute sulfuric acid (50 %, 250 ml) at 110 C. Stirring was continued for 15 min. The reaction mixture was cooled to RT, ice water was added, extracted with ethylacetate, washed with water, brine and dried over NA2SO4. The phenol product obtained upon concentration was purified by column chromatography. Yield 12.0 g, 24.0 %. [00153] K2CO3 (23.84 g, 0.172 mol) was added to 2-chloro-5- nitrophenol (10.0 g, 0.058 mol) in acetonitrile (100 ml) at RT. After cooling to 0 C, methyl iodide (19.6 g, 0.138 mol) was added slowly and the reaction mixture stirred at RT overnight. Water (100 ml) was added and the aqueous layer extracted with ethyl acetate. The organic layer was washed with water, brine and dried over NA2SO4. The product obtained upon concentration was purified by column chromatography to yield the ANISOLE (6.0 g, 55.55%). [00154] 2-CHLORO-5-NITRO ANISOLE (6.0 g, 0.032 mol) in MEOH (45 ml) was added slowly to stannous chloride (15.1 g, 0.08 mol) in conc. HCI (110 ml) at 40 C and the temperature was slowly raised to 50 C. Stirring was continued for 2 h. After cooling to RT, the reaction mixture was basified with 50 % NAOH solution, extracted by ethyl acetate, washed with water, then brine and dried over NA2SO4. 3-METHOXY-4-CHLOROANILINE was obtained upon concentration and was purified further by column chromatography. Yield : 4.0 g, 79.36 %. [00155] To 3-METHOXY-4-CHLOROANILINE (2.0 g, 0.0126 mol) in trichloroethylene (30 ml) was added BC13 (2.18 g, 1 M solution in DCM, 0.0188 mol) AT 0 C. After stirring for 10 min, 4-CYANOPYRIDINE (1.6 g, 0.0153 mol) and AIC13 (2.35 g, 0.018 mol) were added and the temperature was raised to RT, with further stirring for 30 min. The temperature was raised further to 85 C and maintained at the same temperature for 1 h. DCM was distilled off and the solution was stirred at 115 C for 4 h and then at RT over night. 3N HCI was added at RT and the reaction mixture REFLUXED for 1.5 h. The reaction mixture was allowed to cool and made basic using NAOH (6 N), diluted with water and extracted with DCM, washed with water, brine and dried over NA2SO4. The crude title compound was obtained upon concentration and was purified by column chromatography. Yield : 0.50 g, 15 %.

Statistics shows that 13726-14-2 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-3-methoxyaniline.

Reference:
Patent; CHEMOCENTRYX; WO2004/46092; (2004); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7781-10-4, name is 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, 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 7781-10-4, 7781-10-4

General procedure: A typical procedure for the preparation of 3a:2-bromopropane (74 mg, 0.6 mmol) was added to a solution of 1a (92 mg, 0.6 mmol) and K2CO3 (110 mg, 0.8 mmol) in 5 mL DMF at 70 C. According to TLC the reaction went to completion after 4 h. The mixture was extracted with ethyl acetate (3 * 10 mL). The combined organic layers were washed with brine(10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give the crude product 2a, which was added to a solution of amino-phenol(66 mg, 0.6 mmol) and Cs2CO3 (585 mg, 1.8 mmol) in 10 mL DMSO without further purification. After stirring for 6 h at 80 C, the mixture was cooled to room temperature and extracted with ethyl acetate (3 * 10 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give the crude product, which was further purified by column chromatography(petroleum ether/ethyl acetate 2:1) to afford compound 3a as a brown solid(121 mg, 75% over two steps): 1H NMR (300 MHz, CDCl3) delta 8.44 (s, 1H), 7.16 (d, J = 3.6 Hz, 1H), 7.02 (d, J = 8.9 Hz, 2H), 6.73 (d, J = 8.9 Hz, 2H), 6.39 (d, J = 3.6 Hz, 1H), 5.11 (m, 1H), 3.70 (s, 2H), 1.51 (d, J = 6.8 Hz, 6H).; 13C NMR (100 MHz, d6-DMSO) delta 162.5, 151.5, 150.0, 146.3, 142.7, 124.5, 122.2, 114.3, 104.6, 98.0, 46.0, 22.3.; HRMS [M]+ calcd for C15H16N4O268.1324, found 268.1326. The purity of the compound was >98% by HPLC.

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-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Yang; Fang, Jianping; Cai, Haiyan; Xiao, Fei; Ding, Kan; Hu, Youhong; Bioorganic and Medicinal Chemistry; vol. 20; 18; (2012); p. 5473 – 5482;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

933190-51-3, Adding some certain compound to certain chemical reactions, such as: 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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 933190-51-3.

Comparative Example 1 e 8-Bromo-6-chloro-3-iodoimidazo 1 ,2-b]pyridazine A mixture comprising 100 g (430 mmol) 8-bromo-6-chloroimidazo[1 ,2- b]pyridazine which was prepared according to a procedure described in US2007/78136 (WO2007/38314), 145 g N-iodosuccinimide, 5 percent per weight cone, hydrochloric acid and 1 L trichloromethane was heated at reflux for 6 hours. 20 g N-iodosuccinimide were added and heating was continued for additional 3 hours. The precipitate was removed and the filtrate was washed with 1 N sodium hydroxide solution, brine and dried over sodium sulfate. After filtration and removal of solvent diisopropyl ether was added and the residue was stirred at 23 C overnight. The precipitate was filtered off and dried to give 66.6 g (43%) of the title compound.

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 933190-51-3.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WENGNER, Antje, Margret; SIEMEISTER, Gerhard; WO2014/198776; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, 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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, A new synthetic method of this compound is introduced below.

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 (300 MHz, DMSO-d6): delta [ppm]= 7.23 – 7.40 (m, 2H), 7.51 (d, 1 H), 7.59 – 7.67 (m, 2H), 7.77 (d, 1 H), 8.33 – 8.40 (m, 2H).LCMS (Method 1 ): Rt = 1.35 min; MS (ESIpos) m/z = 270 [M+H]+.

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; Bayer Intellectual Property GmbH; EIS, Knut; PUeHLER, Florian; ZORN, Ludwig; SCHOLZ, Arne; LIENAU, Philip; GNOTH, Mark, Jean; BOeMER, Ulf; GUeNTHER, Judith; FANGHAeNEL, Joerg; KORR, Daniel; WO2012/175591; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 1996-29-8

Under an argon gas atmosphere, in the presenceof catalytic amount iodine, to THF (50 mL) suspension of magnesium (1.28 g, 52.5 mmol), THF solutionof 1-bromo-4-chloro-2-fluorobenzene (10.0 g, 47.8mmol) was dropped at 40 (oil bath temperature), to prepare a Grignard reagent. This Grignard reagentwas dropped under -50 to THF solution of diethyl oxalate (8.37g, 57.3mmol), and the mixturewas gradually heated to room temperature andstirred for 18 hours. After completion of the reaction, the reactionsolution was poured into ice and acidified with concentrated hydrochloric acidand extracted with ether (100mL ¡Á 2,50mL ¡Á 1). The organic layer was dried overanhydrous magnesium sulfate and then concentrated under reduced pressure togive orange oily crude product (12.9g). This was purified by silica gel columnchromatography (hexane: ethyl acetate = 10: 1) to give yellow oil of 2-(4-chloro-2-fluorophenyl) -2-oxoethyl acetate (4.17 g, yield: 41%).

Statistics shows that 1996-29-8 is playing an increasingly important role. we look forward to future research findings about 1-Bromo-4-chloro-2-fluorobenzene.

Reference:
Patent; SAGAMI CHEMICAL RESEARCH INSTITUTE; KAKEN PHARMACEUTICAL COMPANY LIMITED; KOBAYASHI, OSAMU; TAKATSUNA, REIKO; NIIKURA, NAOKO; MATSUKAWA, TOMOKO; NAKAMURA, SHINJI; HIRAI, KENJI; KOCHI, SHINICHIRO; KAWANISHI, NAOKI; YAMADA, OSAMU; (75 pag.)JP2016/56157; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics