Author: Jessica.F

Application of 1435-48-9, 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. 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: As a typical experiment, the reaction of the 2-halopyridine (1 mmol), fluorobenzene derivative (2.5 mmol) and PivOK (0.154 g, 1.1 mmol) at 150 C during 16 h in DMA (3 mL) in the presence of PdCl(C3H5)(dppb) (12 mg, 0.02 mmol) (see tables or schemes) under argon affords the arylation product after evaporation of the solvent and filtration on silica gel

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

Reference:
Article; Boyaala, Rabab; Touzani, Rachid; Guerchais, Veronique; Soule, Jean-Francois; Doucet, Henri; Tetrahedron Letters; vol. 58; 33; (2017); p. 3205 – 3208;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 61881-19-4,Some common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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.

10249] To a solution of 6-(6?-azidohexyl)-2,3,4-tri-O-ben- zyl-a/3-D-galactopyranose 18 (400 mg, 0.70 mmol) in CH2C12 (7 mE) was added cesium carbonate (340 mg, 1.04 mmol). To the mixture was added 2,2,2-trifluoro-N-pheny- lacetimidoyl chloride 24 (216 mg, 1.04 mmol) and the reaction mixture was stirred at r.t. for 3.5 h after which it was filtered over celite and washed with CH2C12. The solvent was removed in vacuo and the crude product was purified by flash column chromatography on silica gel (gradient hexanes/ EtOAc1 0:1 – 1:1) to yield the imidate 19 (490 mg, 94%) as a colorless oil. [a]Dt+60.8 (c0.4, CHC13); R1O.8O (Hexanes/EtOAc 2:1); IR (film) vm,x 3064, 2934, 2865, 2094, 1717, 1598, 1454, 1321, 1207, 1099, 1027, 910, 734, 696cm?; ?H NMR (400 MHz, CDC13) oe 7.45-6.60 (m, 20H),5.56 (s, 1H), 4.90 (d, J11.5 Hz, 1H), 4.75 (s, J1.5 Hz, 2H),4.68 (s, J12.4 Hz, 2H), 4.58 (d, J11.6 Hz, 1H), 4.00 (t,J8.7 Hz, 1H), 3.84 (d, J2.4 Hz, 1H), 3.58-3.39 (m, 4H),3.34 (dt, J9.3, 6.5 Hz, 1H), 3.23 (dt, J9.3, 6.5 Hz, 1H), 3.14(t, J6.9 Hz, 2H), 1.52-1.38 (m, 4H), 1.32-1.16 (m, 4H); ?3CNMR (101 MHz, CDC13) oe 138.6, 138.3, 138.2, 128.8, 128.6,128.5, 128.4, 128.4, 128.3, 128.0, 127.9, 127.8, 127.7, 124.3,119.4,82.3,78.3,77.4,77.2,76.8,75.7,74.9,74.6,73.4,73.2,71.4, 68.7, 51.5, 29.7, 28.9, 26.7, 25.8; HR ESI Calcd forC41H45F3N406 [M+Na]: 769.3183. found: 769.3239.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, its application will become more common.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; UNIVERSITAeTSSPITAL BASEL; Seeberger, Peter H.; Stallforth, Pierre; De Libero, Gennaro; Cavallari, Marco; US2015/238597; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, 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. Recommanded Product: 2533-69-9

A round-bottom 3 neck flask was charged with 3,4-diaminobenzenesulfonic acid (8.0 g, 42.5 mmol) and anhydrous MeOH (0.85 L). O-Methyl-1,1,1-trichloroacetimidat was added (2.8 mL, 3.74 g, 21.2 mmol). The resultant suspension was stirred for 24 h at ambient conditions. Additional amount of O-methyl-1,1,1-trichloroacetimidat was added (1.4 mL, 1.87 g, 10.5 mmol) after this time, then reaction mixture was stirred for 72 h days at ambient conditions, heated for 3 h at 50 C. and triethylamine (14 mL, 9.4 g, 93.5 mmol) was added. Stirring was continued at this temperature for 18 h. Then reaction mixture was cooled to 30 C., and an intensive flow of dry HCl was passed through the solution until a precipitate formed. The suspension was filtered off at 40 C., precipitate was washed with MeOH (4¡Á150 mL, stirring of suspension for 10-15 min each turn) and with MeOH-HCl 3.5% solution (100 mL, 1 h of stirring). Product 1H,1’H-2,2′-bibenzimidazole-5,5′-disulfonic acid was pale yellow or colorless, weight 3.5 g, yield 42%. It may contain own hydrochloride as a salt. NMR1 H spectrum (Brucker Avance 300 instrument; solvent d6-dimethyl sulfoxide; delta, ppm; J, Hz): 5.27 br.s (-SO3H in exchange with H2O and NH) 7.73 m (2Ha,2Hb), 8.01 br.s (2Hx). NMR 13C{1H} spectrum (Brucker Avance 300 instrument; solvent d6-dimethyl sulfoxide; delta, ppm): 113.00, 115.41, 123.27, 136.44, 137.60, 142.24, 145.34.

The synthetic route of 2533-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CRYSOPTIX KK; US2010/279122; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 110407-59-5, The chemical industry reduces the impact on the environment during synthesis 110407-59-5, name is 2-Chloro-4-fluorobromobenzene, I believe this compound will play a more active role in future production and life.

Step 1: Synthesis of l-bromo-2-chloro-4-methylsulfanylbenzene. (8)[00392] A solution of l-bromo-2-chloro-4-fluorobenzene (7, 0.50 g, 2.39 mmol) and sodium thiomethoxide (0.17 g, 2.42 mmol) in DMSO (2.5 mL) was stirred at 100 C for 1 h. The reaction mixture was added to 20 mL water with stirring, the aqueous mixture was extracted with ethyl acetate (2 x 20 mL) and the combined organic layers were dried over sodium sulfate, filtered and evaporated in vacuo. The title compound (0.62 g) was obtained as a colorless oil and was used in the next step without further purification.

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-Chloro-4-fluorobromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio, G.; VOLLRATH, Benedikt; WADE, Warren; WO2011/156646; (2011); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1940-27-8, A common heterocyclic compound, 1940-27-8, name is 4-Bromo-2,5-dichloroaniline, molecular formula is C6H4BrCl2N, 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.

General procedure: A mixture of compound (III) (4.2 mmol), the appropriate amine (4.2 mmol) and triethylamine (8.4mmol) in dry acetonitrile was refluxed for 3 hr. The mixture was cooled, poured on crushed ice and filtered. The residue was washed with cold water and dried. The crude product was recrystallized from ethanol to get the titled compounds.

The synthetic route of 1940-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pradeep Kumar; Joshi, Shrinivas D.; Dixit, Sheshagiri R.; Kulkarni; Indian Journal of Heterocyclic Chemistry; vol. 25; 1; (2015); p. 37 – 44;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2106-04-9, These common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, 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 1; 4- (3-CHLORO-2-FLUOROANILINO)-6- [1- (HYDROXYACETYL) PIPERIDIN-4-YLOXY]-7- methoxyquinazoline; HATU (28.9 g) was added to a stirred solution of 4- (3-chloro-2-fluoroanilino)-7- METHOXY-6- (PIPERIDIN-4-YLOXY) quinazoline dihydrochloride (30 g), glycolic acid (5.40 g) and di-isopropylethylamine (44.70 ml) in methylene chloride (900 ml). After 1.5 hours the reaction mixture was washed with sodium hydroxide solution (2M), water and saturated brine. The resulting product was then purified by flash chromatography on silica eluting with 3% MeOH/methylene chloride. The fractions containing the desired product were combined and reduced in vacuo to give the title product as a white solid which was recrystallised from acetonitrile (29.6 g); NMR Spectrum : (DMSO d6) 1.65-1. 81 (m, 2H), 1.99-2. 10 (m, 2H), 3.26- 3.34 (m, 1H), 3.37-3. 47 (m, 1H), 3.60-3. 68 (m, 1H), 3.81-3. 89 (m, 1H), 3.95 (s, 3H), 4.14 (d, 2H), 4.50 (t, 1H), 4.78 (m, 1H), 7.25 (s, 1H), 7.30 (t, 1H), 7.46-7. 55 (m, 2H), 7.88 (s, 1H), 8.40 (s, 1H), 9.55 (s, 1H) ; Mass Spectrum: (M+H) + 460.94. THE 4- (3-CHLORO-2-FLUOROANILINO)-7-METHOXY-6- (PIPERIDIN-4-YLOXY) quinazoline dihydrochloride starting material was prepared as follows: 6-Acetoxy-4-chloro-7-methoxyquinazoline, (Example 25-5 in WO01/66099 ; 10. 0G, 39.6 mmole) was added in portions to a stirred 7N methanolic ammonia solution (220 ml) cooled to 10C in an ice/water bath. After stirring for one hour the precipitate was filtered, washed with diethylether and dried thoroughly under high vacuum to give 4-chloro-6- hydroxy-7-methoxyquinazoline (5.65 g, 67.8 %); NMR Spectrum: (DMSO d6) 3.96 (s, 3H); 7.25 (s, 1H); 7.31 (s, 1H); 8.68 (s, 1H); Mass Spectrum : (M+H) + 211 Di-tert-butylazodicarboxylate (9.22 g) in methylene chloride (20 ml) was added slowly to a stirred suspension of 4-chloro-6-hydroxy-7-methoxyquinazoline (5.63 g), 4-hydroxy-1- tert-butoxycarbonylpiperidine (8.06 g) and triphenylphosphine (10.5 g) in methylene chloride (100 ml) at 5C under an atmosphere of nitrogen. The reaction mixture was allowed to warm to room temperature for 16 hours. The reaction mixture was then evaporated under vacuum and adsorbed onto silica and the product was eluted with isohexane/ethyl acetate/triethylamine (75/24/1 followed by 70/29/1). The fractions containing the desired product were combined and evaporated under vacuum to give tert-butyl 4- [ (4-CHLORO-7-METHOXYQUINAZOLIN-6- yl) oxy] piperidine-l-carboxylate as a white solid (10.3 g) ; IH NMR SPECTRUM : (DMSO d6) 1.40 (s, 9H), 1.56-1. 69 (m, 2H), 1.93-2. 04 (m, 2H), 3.20-3. 31 (m, 2H), 3.60-3. 70 (m, 2H), 4.00 (s, 3H), 4. 89 (m, 1H), 7.45 (s, 1H), 7.50 (s, 1H), 8.86 (s, 1H) ; Mass Spectrum : (M+H) + 394. 4. 0M HC1 in Dioxane (4.0 ml) was added to a suspension of tert-butyl 4- [ (4-chloro-7- methoxyquinazolin-6-yl) oxy] PIPERIDINE-1-CARBOXYLATE (2.62 g) and 3-chloro-2-fluoroaniline (1.08 g) in iso-propanol (50 ml). The reaction mixture was stirred and heated at 100C for 2 hours. The yellow precipitate was filtered hot and washed with iso-propanol followed by diethylether and dried under vacuum to give 6- (PIPERIDIN-4-YLOXY)-4- (3-CHLORO-2- fluoroanilino) -7-methoxyquinazoline as a di-hydrochloride salt (2.38 g) ; 1H NMR SPECTRUM (DMSO D6) 1.84-1. 99 (m, 2H), 2.22-2. 33 (m, 2H), 3.12-3. 33 (m, 4H), 4.00 (s, 3H), 5. 08 (m, 1H), 7.34 (t, 1H), 7.40 (s, 1H), 7.50 (t, 1H), 7.62 (t, 1H), 8.80 (s, 1H), 8. 84-8. 94 (m, 2H), 8.99-9. 11 (m, 1H); Mass Spectrum: (M+H) + 403.

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/12290; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 4090-55-5, 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 4090-55-5 as follows.

(Synthesis of phosphorus compound (1)); The flask accommodating the post-reaction solution containing intermediate 2 was filled with 121. 4 g (1.2 mol) of triethylamine, 1.85 g (0.015 mol) of 4-(dimethylamino) pyridine, and 420 g of 1, 2-dichloroethane. While the mixed solution was stirred, a mixed solution of 177.1 g (0.96 mol) of material 1 and 450 g of 1,2-dichloroethane was added thereto at 20C over 2 hours. After that, the substances were reacted at the same temperature (20C) for 8 hours. The obtained post-reaction solution was neutralized at room temperature using an aqueous solution of hydrochloric acid in an amount corresponding to the excess amount of triethylamine. The resultant solution was kept still so as to be separated into different layers. Then, the organic layer was neutralized using an aqueous solution of sodium hydrogen carbonate. The organic layer was then washed with water twice. The obtained organic layer was dried by anhydrous magnesium sulfate. Toluene was added to the filtrate, and recrystallization was performed. Thus, 171. 4 g of phosphorus compound (1) was obtained. Phosphorus compound (1) had a purity measured by GPC (gel permeation chromatography) of 100% by area. The yield was 54.4%.

According to the analysis of related databases, 4090-55-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DAIHACHI CHEMICAL INDUSTRY CO., LTD.; EP1632497; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 210532-25-5, 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. 210532-25-5 name is 3,5-Difluorobenzene-1-sulfonyl 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.

General procedure: A mixture of appropriate aryl sulfonyl chloride (0.6mmol), 48 (179.7mg, 0.5mmol), Cs2CO3 (325mg, 1mmol) and acetone (5mL) was stirred at room temperature for overnight. The mixture was filtered to remove Cs2CO3 and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Difluorobenzene-1-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Article; Wang, Guangcheng; Li, Chunyan; He, Lin; Lei, Kai; Wang, Fang; Pu, Yuzi; Yang, Zhuang; Cao, Dong; Ma, Liang; Chen, Jinying; Sang, Yun; Liang, Xiaolin; Xiang, Mingli; Peng, Aihua; Wei, Yuquan; Chen, Lijuan; Bioorganic and Medicinal Chemistry; vol. 22; 7; (2014); p. 2060 – 2079;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 118-69-4,Some common heterocyclic compound, 118-69-4, name is 2,6-Dichlorotoluene, molecular formula is C7H6Cl2, 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.

5 g of catalyst, as described in examples 3 and 4, was loaded in the reactor along with the diluent corundum particles (1: 1 by weight) and the reaction was performed under the following conditions. A reaction temperature of 350 to [400C] was used, and the GHSV comprised between 650-750 [H-1.] The contact time consisted of 4.8 to 5.5 seconds. The mole ratio of 2,6-DCT : H20 : NH3: air: N2 was 1: 15: 3-4: 21, the molar concentration of 2,6- DCT was 2.4 % and the ratio of [0/NH3] was 1. [1 %.]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Dichlorotoluene, its application will become more common.

Reference:
Patent; TESSENDERLO CHEMIE S.A.; WO2003/101939; (2003); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. Computed Properties of C6H3BrClN3

To a solution of 3-bromo-6-chloro-imidazo[1 ,2-b]pyridazine (2.40 g, 10.35 mmol) in 30 ml_ of THF was added EtMgBr (1 M in THF, 12.43 ml_, 12.42 mmol) solution at rt. The solution was stirred for 30 min and a solution of 5,7-difluoroquinoline-6-carbaldehyde (2.0 g, 10.35 mmol) in 1 O mL of THF was added. The resulting mixture was stirred at rt for additional 2 h and then quenched with 50 ml_ of NH4CI solution. The solution was extracted with EtOAc and the combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated in vacuo to afford 3.48 g (97%) of the title compound. LCMS (method B): [MH]+ = 347, tR = 1 .23 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13526-66-4, its application will become more common.

Reference:
Patent; NOVARTIS AG; DAI, Miao; FU, Xingnian; HE, Feng; JIANG, Lei; LI, Yue; LIANG, Fang; LIU, Lei; MI, Yuan; XU, Yao-chang; XUN, Guoliang; YAN, Xiaoxia; YU, Zhengtian; ZHANG, Ji, Yue; WO2011/20861; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics