Category: chlorides-buliding-blocks

126764-17-8, 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. 126764-17-8 name is 1-Chloro-6,6-dimethylhept-2-en-4-yne, 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.

N-Methyl-l-naplithylmethylamine (100 g) was dissolved in water (250 ml). Sodium hydroxide (41.50 g) was dissolved in water (120 ml) and this aqueous sodium hydroxide solution was added to N-Met^yl-I-napththyliriethylatnine solution at 20-400C. The reaction mass was heated to 90-950C and l-chloro-6,6- dimethyl-hept-2-ene-4-yne (96 g, crude viscous oily mass having chromatographic purity by GC 92.40%, as obtained in Step A) was added at 90- 100C. The reaction mass was stirred at 90-1000C for 2 hrs and then cooled to room temperature. Methylene chloride (400 ml) was added and organic layer separated. The methylene chloride extract was washed with water (150 ml). The washed methylene chloride solution was stirred with 300 ml dilute hydrochloric acid at room temperature for 1 h. The methylene chloride layer was washed with water (100 ml) and treated with carbon (4 g) at room temperature. The methylene chloride was stripped to get a residue. The residue was refluxed for 30 min with ethyl acetate (600 ml). The product slurry was cooled to room temperature and stirred for 30 min. Product was filtered and washed with preheated ethyl acetate (160 ml, 40-450C). Product was dried at 55-600C under reduced pressure for 4 h to yield 104 g of Terbinafne hydrochloride, containing 1087 ppm of impurity of Formula IV.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Chloro-6,6-dimethylhept-2-en-4-yne, and friends who are interested can also refer to it.

Reference:
Patent; AUROBINDO PHARMA LTD; WO2007/52089; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., 13526-66-4

mixture of 2.0 g (16.8 mmol) furo[3,2-b]pyridine and anhydrous THF (100 mL) was cooled to -78 C. 10.1 mL (25.2 mmol) of a 1 .6 M solution of n-butyllithium in hexane was added and the resulting mixture stirred for 1 h at -78 C. 6.8 mL (25.2 mmol) of tributyltin chloride was added at -78 C. The cooling bath was removed and the reaction was stirred at room temperature over night. Methanol was carefully added and the solvent evaporated. The obtained residue was purified by flash chromatography to yield 7.4 g of crude product of the corresponding 2-stannylbenzofurane, which was used without further purification. In an inert atmosphere, 3.0 g (12.9 mmol) of 3-bromo-6-chloro-imidazo[1 ,2-b]- pyridazine, 6.85 g (16.8 mmol) of the crude 2-stannylfuro[3,2-b]pyridine, 246 mg (1 .29 mmol) copper (I) iodide and 453 mg (0.645 mmol) bis(triphenylphosphine) palladium(ll)chloride in 100 mL of THF was stirred over night at 85 C in a sealed pressure tube. The solvent was evaporated, the obtained solid was digested in dichloromethane/methanol and filtered off. The solid was washed with methanol and hexane to give 2 g of the title compound as solid material. 1H-NMR (300 MHz, DMSO-de), delta [ppm]= 7.35-7.45 (1 H), 7.57-7.64 (1 H), 7.65-7.70 (1 H), 8.08-8.15 (1 H), 8.40-8.47 (1 H), 8.47-8.52 (1 H), 8.54-8.62 (1 H). LCMS (Method 3): Rt = 0.91 min; MS (ESIpos) m/z = 271 [M+H]+.

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; BAYER PHARMA AKTIENGESELLSCHAFT; ZORN, Ludwig; EIS, Knut; SCHULZE, Volker; SUeLZLE, Detlev; PUeHLER, Florian; LIENAU, Philip; BOeMER, Ulf; PETERSEN, Kirstin; HAeGEBARTH, Andrea; WO2014/118135; (2014); A1;,
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. 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, A new synthetic method of this compound is introduced below., 6579-54-0

2,6-Dichloro-3-nitrobenzenesulfonic acid Lithium hydroxide hydrate (12.64 g, 0.301 mol) was added to a solution of 2,6-dichlorobenzenesulfonyl chloride (35.53 g, 0.146 mol) in MeOH (600 mL) and the reaction was allowed to stir at room temperature for 3 hr. The reaction mixture was filtered to remove suspended solids and then concentrated. The resulting solid was dried in vacuo overnight to remove any residual MeOH. The solid was then dissolved in H2SO4 (300 mL) and chilled in an ice bath. A solution of H2S04 (35 mL) and HNO3 (13.2 mL) was slowly added to the above reaction over 90 min. The reaction was allowed to warm up to room temperature overnight and then slowly poured into ice water (1200 mL) and extracted with EtOAc. The combined organic layers were dried (MgSO4) and concentrated to yield 2,6-dichloro-3-nitrobenzenesulfonic acid (44.35 g, 99%) as the dihydrate. EI-MS (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; SmithKline Beecham Corporation; US6500863; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, 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 94-97-3, 94-97-3

General procedure: 1-phenylbutane-1,3-dione 1a (0.2 mmol, 32.4 mg), 1H-benzo[d][1,2,3]triazole 2a (0.2 mmol, 23.8 mg), N-bromosuccinimide (NBS) (39.2 mg, 1.2 equiv), KOtBu (44.8 mg, 2 equiv) and EtOAc (2 mL) were added to a flask with a magnetic stirring bar. The resulting mixture was stirred for 6 h at 60 oC. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 5/1-2/1 as eluent) to give product 3a and 4a as light yellow and pink solids. The identity and purity of the products was confirmed by 1H and 13C NMR spectroscopic analysis

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, 5-Chloro-1H-benzo[d][1,2,3]triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Wen-Lin; Li, Ji-Hui; Meng, Xu; Tang, Dong; Guo, Shuai-Bo; Chen, Bao-Hua; Tetrahedron Letters; vol. 54; 4; (2013); p. 295 – 299;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, I believe this compound will play a more active role in future production and life. 1871-57-4

Part 2; A mixture of (2S)-benzylamino-succinic acid 1-benzyl ester 4-tert-butyl ester (12.1 g, 32.6 mmol), K2CO3 (14 g, 3 equiv.), NaI (3.0 g, 20 mmol) and 1-chloro-2-chloromethyl-1- propene (5.1 g, 40.8 mmol) in MeCN (150 mL) was stirred at 81C for 16 h. After cooling, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification by Combiflash (hexane and ethyl acetate: gradient 0 to 8% during 12 min) afforded (2S)- [benzyl- (2-chloromethyl-allyl)-amino]-succinic acid 1-benzyl ester 4-tert-butyl ester (8.7 g, 58%). MS (ESI): 458 (M + H+).

The chemical industry reduces the impact on the environment during synthesis 1871-57-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; INCYTE CORPORATION; WO2005/37826; (2005); A1;,
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. 823-57-4, name is 2-Bromo-5-chloroaniline, A new synthetic method of this compound is introduced below., 823-57-4

Intermediate 129 4-Chloro-4′-fluorobiphenyl-2-amine 2-Bromo-5-chloroaniline (CAS 823-57-4; 5 g), 4-fluorophenylboronic acid (3.56 g) and cesium carbonate (31.6 g) were combined in THF (70 ml) and water (35 ml). The mixture was degassed by bubbling argon through the solution. After addition of [Iota, – bis(diphenylphosphino)ferrocene]dichloropalladium(II) (886 mg) the reaction mixture was stirred 1 h at 80 ¡ãC in a sealed tube. The reaction mixture was diluted with EtOAc, washed with water, dried over Na2S04, evaporated and purified by chromatography (silica gel, 0percent to 30percent EtOAc in heptane). The product was finally bulb-to-bulb distilled at 0.3 mbar and 120-130 ¡ãC oven temperature to give the title compound (5.07 g) as a light yellow liquid. In analogy to the synthesis of Intermediate 129, the following intermediates were prepared:

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BUETTELMANN, Bernd; CECCARELLI, Simona M.; CONTE, Aurelia; KUEHNE, Holger; KUHN, Bernd; NEIDHART, Werner; OBST SANDER, Ulrike; RICHTER, Hans; WO2014/146994; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 6579-54-0 name is 2,6-Dichlorobenzenesulfonyl chloride, 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. 6579-54-0

a) 2-[(Cyclopropylcarbamoyl)amino]-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate may be prepared in the following manner:To a suspension of 300 mg of 1-cyclopropyl-3-(5-hydroxy-1H-benzimidazol-2-yl)urea in 100 cm3 of acetone are added 186 mg of triethylamine and 349 mg of 2,6-dichlorobenzenesulfonyl chloride. After stirring overnight at a temperature in the region of 20 C., 90 mg of 2,6-dichlorobenzenesulfonyl chloride are added and the mixture is stirred for a further 24 hours. The reaction medium is evaporated to dryness under reduced pressure (2 kPa). The residue is taken up in 50 cm3 of water and then extracted with three times 40 cm3 of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure (0.5 kPa). After flash chromatography on a column of silica [eluent: dichloromethane/methanol (96.5/3.5 by volume)], the product obtained is solidified in 10 cm3 of diethyl ether and then filtered off, washed with three times 5 cm3 of diethyl ether and dried under reduced pressure over phosphorus pentoxide. 130 mg of 2-[(cyclopropylcarbamoyl)amino]-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate are obtained in the form of a cream-coloured powder, the characteristics of which are as follows:Melting point: melting at 160-165 C. (Koefler block)1H NMR spectrum at 400 MHz: 0.47 (m, 2H); 0.68 (m, 2H); 2.62 (m, 1H); 6.75 (dd, J=2.5 and 8.5 Hz, 1H); 7.09 (broad m, 1H); 7.24 (broad m, 1H); 7.30 (broad d, J=8.5 Hz, 1H); from 7.68 to 7.79 (m, 3H); 9.82 (broad m, 1H); 11.75 (broad m, 1H)Mass spectrum: MS (ES+): m/z=441 [MH+]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichlorobenzenesulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; AVENTIS PHARMA S.A.; US2008/194555; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., 27139-97-5

Example 4 This example illustrates the preparation of a compound having Formula I, 4′,4″-(diphenylmethylene)N,N-bis(3-(biphenylen-1 -yl-4- methyl)phenyl)aniline), Compound 3 below. Compound 3 a. 5-chloro-3′-phenyl-2-methylbiphenyl To a 2 L round bottle flask equipped with reflux condenser, stir bar, nitrogen feed, and oil bath were added 2-bromo-4-chlorotoluene (20.67 g, 98.59 mmol), 3-biphenylboronic acid (20.50 g 103.52 mmol), sodium carbonate (158 mL, 31 5 mmol), Aliquat 336 (4.00 g) and toluene (600 mL). Solution was purged with nitrogen for 20 minutes before addingtetrakis(triphenylphospine)palladium(0) (1 .14 g, 0.98 mmol) and purged for another 10 minute. The reaction was then heated under nitrogen for 18 hour. After cooing to ambient temperature, the organic phase was separated, washed with 1 0percent HCI (200mL), water (200mL) and saturated brine (200mL). This solution was dried with magnesium sulfate (50 g) for 3 hour and the solvent was removed by rotary evaporation. The crude product was filtered, washing with with hexane. Product containing fractions were identified by UPLC and collected. Low boiling point impurities and solvents were removed by Kruger-Rohr distillation to give the product as colorless oil (20.2 g, 77percent).

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; E. I. du Pont de Nemours and Company; WANG, Ying; WU, Weishi; DOBBS, Kerwin, D.; WO2011/49953; (2011); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene, molecular formula is C6H3BrCl2, 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. 56961-77-4

EXAMPLE 10 6-(2,3-Dichlorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 109, structure 4 of Scheme II, where R1 =2,3-dichlorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9). From Compound 9 (68.0 mg, 0.21 mmol) and commercially available 2,3-dichlorobromobenzene (40.1 mg, 0.18 mmol, Lancaster) was obtained a crude product which was isolated and purified by reverse phase HPLC (ODS column, 97% methanol/water, 3.0 mL/min) to afford 20 mg (29%) of Compound 109. Data for Compound 109: 1 H NMR (400 MHz, CDCl3) 7.39 (dd, J=8, 1.6, 1H), 7.19 (dd, J=16, 8, 1H), 7.23 (dd, J=4, 1.6, 1H), 7.11 (d, J=1.6, 1H), 7.05 (dd, J=8, 1.6, 1H), 6.46 (d, J=8, 1H), 5.34 (s, 1H), 3.82 (br s, 1H), 1.99 (s, 3H), 1.32 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 56961-77-4, its application will become more common.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5696127; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-29-8, name is 1-Bromo-4-chloro-2-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 1996-29-8, 1996-29-8

In a 200 mL three-necked flask, 4.3 g (crude)2,6-dihydroxy-1,5-diphenylnaphthalene,8.6 g (0.42 mol) of 1-bromo-4-chloro-2-fluorobenzene, and 13 g (41 mmol) of cesium carbonate.To this mixture, 70 mL of N-methyl-2-pyrrolidone was added,The mixture was degassed by stirring while reducing the pressure.After degassing, the mixture was stirred at 120 C. for 13.5 hours under a nitrogen stream. After stirring, 2.9 g (14 mmol) of 1-bromo-4-chloro-2-fluorobenzene was added and the mixture was stirred at 120 C. for 13.5 hours under a nitrogen stream.After stirring, water was added to this mixture, and after ultrasonic irradiation, filtration was carried out to obtain a solid. The obtained solid was washed with water and ethanol. This solid was purified by silica gel column chromatography (developing solvent: toluene). This solid was recrystallized from toluene / ethanol to obtain 6.3 g of a pale yellow solid in a yield of 66%. The synthesis scheme of Step 2 is shown below.

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, 1-Bromo-4-chloro-2-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Semiconductor Energy Laboratory Ltd.; Takeda, Kyoko; Ozaka, Harue; Seo, Tetsushi; Suzuki Tsune Toku; Hashimoto Naoaki; Takida Yuu Kai; (218 pag.)JP6339749; (2018); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics