Month: September 2021

Synthetic Route of 7149-75-9, 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. 7149-75-9, name is 4-Chloro-3-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a refluxing slurry of disodium carbonate (0.9 g. 0.01 mol) in 10 mL MeOH wasadded simultaneously a solution of 1,5-dichloropentan-3-one (0.93 mL, 0.01 mol) in 5 mL MeOH and a solution of 4-chloro-3-methylaniline (1 g, 0.01 mol) in 5 mL MeOH dropwise over 10 mins. The reaction was allowed to reflux for a further 2.5 h, then allowed to cool and concentrated, poured into water (10 mL), and extracted with DCM (2 x lOmL). The combined organics were dried over MgSO4 and concentrated to yield 1.38 g free flowing orange/brown oil. The crude product was purified using column chromatography (Biotage, 50 g SNAP KP-SIL, 10 -80percent EtOAc in heptane, 10 CV) to yield the title compound as a light yellow free-flowing liquid (890 mg, 86percent purity, 48percent).1H NMR (500 MHz, Chloroform-d) delta 7.22 (d, J = 8.7 Hz, 1 H), 6.83 (d, J = 2.9 Hz, 1H), 6.74 (dd, J = 8.7, 3.0 Hz, lH), 3.56 (t, J = 6.1 Hz, 4H), 2.55 (t, J = 6.1 Hz, 4H), 2.35 (s, 3H). LCMS Method D: rt 1.33 min, 91 percent; m/z 223.95 (MH+)

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-3-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; EVOTEC INTERNATIONAL GMBH; GAMPE, Christian, M.; KAHNE, Daniel, Evan; KAHNE, Suzanne, Walker; QIAO, Yuan; EAST, Stephen; PARKES, Alastair, L.; SOUTHEY, Michelle; HUNTER, James; WHITTAKER, Mark; ARTHUIS, Martin; (359 pag.)WO2016/191658; (2016); A1;,
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Electric Literature of 64628-73-5, 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. 64628-73-5, name is 3-Chloro-4-(trifluoromethoxy)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-Bromo-7-fluoro-1H-indole-2-carboxylic acid ethyl ester (200 mg, 0.7 mmol) was dissolved in toluene (16 mL), and Pd2 (dba) 3 (64 mg, 0.07 mmol) and Davephos (55 mg) were sequentially added. , 0.14mmol) and K3PO4 (401mg, 2.1mmol, 2.1mLH2O), after stirring well, 3-methoxy-5-trifluoromethylaniline (444mg, 2.10mmol) in toluene (4mL) was added, argon Under protection, the reaction was refluxed overnight with a small amount of starting material remaining. Cool to room temperature, concentrate, add EA (30mL) to dissolve the residue, 6N hydrochloric acid (10mL × 2), wash with saturated brine (20mL × 3), wash with water (20mL × 2), column chromatography (P / E = 20: 1 10: 1) to obtain 225 mg of off-white solid, yield 81.2%, melting point: 143-145 C.

The synthetic route of 3-Chloro-4-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Cui Guonan; Lai Fangfang; Zhou Jie; Ji Ming; Wang Xiaoyu; Du Tingting; Li Ling; Jin Jing; (144 pag.)CN110483366; (2019); A;,
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Related Products of 627-42-9, These common heterocyclic compound, 627-42-9, name is 2-Methoxyethyl chloride, 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 4-(2-Methoxyethoxy)-benzaldehyde 219.8 g of 4-hydroxybenzaldehyde were stirred with 270 g of potassium carbonate and 1134 g of 2-chloroethyl methyl ether in a 3 l autoclave for 12 hours at 150 C. Filtration, washing with 46.1 g of 2-chloroethyl methyl ether and removal by distillation of the excess 2-chloroethyl methyl ether as in Example 1, gave 319.9 g of crude product as red-brown liquid and 819.2 g of 2-chloroethyl methyl ether with a purity of 99.4% (GC).

The synthetic route of 627-42-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Giffels, Guido; Dreisbach, Claus; US2001/14697; (2001); A1;,
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Application of 933190-51-3, 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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-ethylpyridin-2-amine (394 mg, 3.23 mmol) in DMF (8 mL) was added NaH (129 mg, 60% dispersion in mineral oil, 3.23 mmol) under N2 atmosphere at room temperature and stirred for another 0.5 h. To this mixture was added 8-bromo-6-chloroimidazo[1,2-b]pyridazine (0.3 g, 1.3 mmol). After 20 h stirring at room temperature, saturated NH4Cl solution was added and the reaction mixture was extracted with ether (200 mL) and washed with water (2×50 mL), then brine (2×50 mL). After drying and filtration, it was concentrated to afford 6-chloro-N-(5-ethylpyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (785 mg, crude) as a yellow solid that was used directly without further purification. LC-MS: [M+1]+=274, tR=1.726 min.

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:
Patent; Hoffmann-La Roche Inc.; Hermann, Johannes Cornelius; Kuglstatter, Andreas; Lucas, Matthew C.; Padilla, Fernando; Wanner, Jutta; Zhang, Xiaohu; US2013/109661; (2013); A1;,
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Application of 115843-99-7, The chemical industry reduces the impact on the environment during synthesis 115843-99-7, name is 4-Bromo-3-chloro-2-fluoroaniline, I believe this compound will play a more active role in future production and life.

Anhydrous DMF (60 ml_) is added to a flask charged with bromide 9a (5.00 g, 22.2 mmol), Jb/s-(pinacolato)diborane (8.48 g, 33.4 mmol) and potassium acetate (6.35 g, 66.8 mmol) and the resulting suspension is deoxygenated by bubbling a stream of N2 gas through the mixture for 45 min. 1 ,1′-bis(diphenylphosphino)ferrocene (2.73 g, 3.34 mmol) is then added and the mixture is deoxygenated for approximately a further 5 min and is then heated to 950C. After 16 h, the dark reaction mixture is cooled, extracted with EtOAc (500 ml. and 300 ml.) and washed with 1:1 water/brine (600 mL) and brine (600 ml_). The combined extracts are dried over anhydrous MgSO4, filtered and evaporated to a black syrup which is purified by flash column chromatography (EtOAc / hexane) to afford the boronate 9b as white solid contaminated with <25 % of the diboron reagent (4.24 g, 62% yield). 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-3-chloro-2-fluoroaniline, other downstream synthetic routes, hurry up and to see. Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; WO2009/62289; (2009); 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 56961-77-4 as follows. Formula: C6H3BrCl2

Under a nitrogen atmosphere, and added at 80 will have diphenylamine (37.5g),1- bromo-2,3-dichlorobenzene (50.0g), Pd-132 (Johnson Matthey) (0.8 g of ), NaOtBu(32.0g) and xylene (500ml) was heated in a flask and stirred for 4 hours, the temperature was raised to 120 up, and further heated with stirring for 3 hours. Thereaction mixture was cooled until room temperature, water and ethyl acetate to carry outa liquid. Then, the use of silica gel column chromatography (eluent: toluene / heptane =1/20 (volume ratio)) to be purified, is obtained 2,3-dichloro -N, N- diphenyl aniline(63.0g) .

According to the analysis of related databases, 56961-77-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kwansei Gakuin School Corporation; Tian, Shanzuoci; Zhong, Zhongzongyiliang; Zhong, Daoguiyi; Ping, Jingdagui; Xiao, Yeyangping; Zhi, Lianyizhi; Ni, Jingping; Song, Xiawusi; Sheng, Tianlizhao; (405 pag.)CN105431439; (2016); A;,
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Reference of 210532-25-5, These common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, 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.

A mixture of 1 (800 mg, 2.14 mmol) and dibutyltin dichloride (65 mg,0.21 mmol) in THF (13 mL) was stirred for 10 min at rt before 3,5-difluorobenzenesulfonyl chloride (500 mg, 2.35 mmol) dissolved in THF (2 mL)and 1,1,2,2,6-pentamethylpiperidine (0.77 mL, 4.27 mmol) were added underN2 atmosphere, and the resulting solution was stirred at rt o.n. The reactionwas quenched with sat. aq. NH4Cl followed by evaporation of the solvent; theresidue was diluted with CH2Cl2 and washed with water and brine. The organicphase was dried and evaporated. The obtained residue was dissolved inacetic anhydride (10 mL) and pyridine (10 mL) and stirred at rt o.n. An amorphouswhite solid was obtained after evaporation of the solvents to give crude2b, which was used directly in the following inversion. 1H NMR (CDCl3): delta7.47 (d, J = 8.1, 2H, Ph), 7.39-7.29 (m, 8H, Ph), 7.06 (d, J = 8.1, 2H, Ph), 5.38 (s, 1H, CH), 5.22 (t, J = 9.8, 1H, H-2), 4.82 (dd, J = 9.7, 3.6, 1H, H-3),4.61 (d, J = 9.8, 1H, H-1), 4.38 (m, 2H, H-4 and H-6), 4.01 (d, J = 12.5, 1H,H-6), 3.57 (s, 1H, H-5), 2.32 (s, 3H, CH3), 2.01 (s, 3H, Ac). 13C NMR (CDCl3): delta169.0, 137.1, 134.7, 129.7, 129.4, 128.4, 128.3, 126.6, 126.2, 111.1, 101.3, 85.0,80.5, 74.2, 69.5, 69.0, 66.5, 21.4, 20.9. HRMS calcd for [C28H26F2O8S2Na]+,615.0935; found: 615.0939.

Statistics shows that 3,5-Difluorobenzene-1-sulfonyl chloride is playing an increasingly important role. we look forward to future research findings about 210532-25-5.

Reference:
Article; Peterson, Kristoffer; Weymouth-Wilson, Alex; Nilsson, Ulf J.; Journal of Carbohydrate Chemistry; vol. 34; 8; (2015); p. 490 – 499;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2106-02-7, name is 2-Chloro-4-fluoroaniline, molecular formula is C6H5ClFN, 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 2-Chloro-4-fluoroaniline

Compound 17 (1.76 g, 10 mmole) was added to a solution of the 2-chloro-4- fluoroaniline (1.45 g, l0mmole) and pyridine (2 mL) in 15 mL of dichioromethane at 0C. The reaction mixture was allowed to warm to room temperature, and continued to stir at room temperature for 12 hours. The reaction mixture was quenched with water (20 mL), and extracted with dichloromethane (20 mL). The organic layer was separated and washed with HCI (0.4N, 10 mL) and brine, and concentrated to give the desired solid Compound 18 (2.8 g, 98%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2106-02-7, its application will become more common.

Reference:
Patent; TAIWANJ PHARMACEUTICALS CO., LTD; YANG, Syaulan S.; LEE, Kuang-Yuan; LIU, Meng-Hsien; HSIAO, Ming-Yu; PENG, Huang-Kai; WANG, Chiung-Wen; WU, Edwin SC; CHIU, Peter JS; (77 pag.)WO2018/156297; (2018); A1;,
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Synthetic Route of 210532-25-5, 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 210532-25-5 as follows.

1-(ethylsulfonyl)-3-fluorobenzene A stirred mixture of 3-fluorobenzenesulfonyl chloride (0.973 g, 5.00 mmol), sodium bicarbonate (0.84 g, 10.0 mmol), and sodium sulfite (1.16 g, mmol) was heated in water (7 mL) at 95-100 C. for 1 h under nitrogen. The reaction was cooled to ~50 C., treated with (nBu)4NBr (100 mg) and ethyl iodide (2.5 mL) and heated at 70 C. for 18 h. The reaction was cooled, treated with water (10 mL) and extracted with dichloromethane (3*15 mL). The extracts were dried with MgSO4 and concentrated in vacuo. Chromatography on silica gel eluding with an ethyl acetate:hexane gradient of 10:90 to 40/60 gave the title compound as a colorless oil (878 mg). MS (ES) m/z 189.0. Intermediates 2 to 11; 13-14Prepared according to a procedure similar to that described for Intermediate 1, using the appropriate halogenated arylsulfonylchloride and alkylating agent R-LG, and eluting with an appropriate eluent. Intermediate 31,3-difluoro-5-(methylsulfonyl)benzene; MS (EI) m/z 192.

According to the analysis of related databases, 210532-25-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bernotas, Ronald Charles; Ullrich, John William; Travins, Jeremy Mark; Wrobel, Jay Edward; Unwalla, Rayomand Jal; US2010/273816; (2010); A1;,
Chloride – Wikipedia,
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These common heterocyclic compound, 89794-02-5, name is 4-Bromo-2-chlorotoluene, 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 89794-02-5

General procedure: 10.0 mmol of the specified boronic ester (I; R1), 30.0 mmol of magnesium turnings and 5.0 mmol of the salt (II) are suspended in a mixture of 3.40 g of anhydrous toluene and 0.73 g of anhydrous tetrahydrofuran in a dry four-neck flask under a nitrogen atmosphere with a mechanical stirrer, thermometer, metal condenser and pressure-equalized dropping funnel, and stirred vigorously for 30 min. The appropriate haloaromatic (III, R4) is added to this solution, at first in undiluted form, until the onset of exothermicity signals the start of the reaction. The remaining total amount of 30.6 mmol of haloaromatic is diluted with 10.0 g of anhydrous toluene and 10.0 g of anhydrous tetrahydrofuran and added dropwise at such a rate that the internal temperature does not exceed 45 C. On completion of addition, the reaction mixture is heated at reflux for 1 h or until the dissolution of the magnesium was complete. The resulting suspension is discharged onto 50 g of ice-water, and the resulting solids are isolated, washed with cold water and dried under reduced pressure. The composition of Examples 77-91 and selected physical properties are summarized in Table 3.

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

Reference:
Patent; Covestro Deutschland AG; ROeLLE, Thomas; BERNETH, Horst; HOeNEL, Dennis; BRUDER, Friedrich-Karl; (34 pag.)US2019/276479; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics