Author: Jessica.F

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 2106-04-9 as follows. HPLC of Formula: C6H5ClFN

Example 3; Step 1; A round bottom flask was charged with 1 eq of 3-chloro-2-fluoroaniline (3A), 1-methyl-2-pyrrolidinone (about 1.5 M 3A in NMP), 2.2 eq of sodium cyanide, and 1.35 eq of nickel(II) bromide at RT under N2. The concentration was halved by the introduction of additional NMP under N2 and the solution was gently warmed to 200+/-5 C. and stirred for 4 days under N2. The reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with 30 volumes of tert-butyl methyl ether (MTBE) and filtered through celite. The celite pad was then rinsed with 10 volumes of MTBE. The organics were washed with 40 volumes of brine, 2×40 volumes of water and 40 volumes of brine. The combined organics were dried over sodium sulfate and concentrated to afford a brown solid, which was dried under vacuum (-30 in Hg) at 40 C. for 8 hours to afford the compound of Formula 3B (71% yield).

According to the analysis of related databases, 2106-04-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Morgan, Bradley Paul; Muci, Alex; Lu, Pu-Ping; Kraynack, Erica Anne; Tochimoto, Todd; Morgans, David J.; US2006/14761; (2006); A1;,
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Application of 14862-52-3, 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. 14862-52-3, name is 3,5-Dibromochlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 1,3-dibromo-5-chlorobenzene (800 mg, 2.96 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (600 mg, 2.96 mmol) in 1,4-dioaxane (15 mL) K2CO3 (1.2 g, 8.80 mmol) was added and the mixture was degassed with argon for 20 minutes. Pd (PPh3)4 (102 mg, 0.08 mmol) was added to reaction mixture and degassed for another 20 minutes. The reaction mixture was refluxed under stirring for 8 hours and then filtered through celite pad. The filtrate was concentrated and the residue was purified by column chromatography on silica (100-200 mesh) eluting with 15% ethyl acetate in petroleum ether to afford the title compound as white solid (400 mg, 50 %). 1H NMR: (300 MHz, CDCl3) delta 8.70 (dd, J = 4.5, 1.5 Hz, 2H), 7.65-7.64 (m, 1H), 7.59-7.58 (m, 1H), 7.54-7.53 (m, 1H), 7.45 (dd, J = 4.2, 1.5 Hz, 2H); ESIMS: m/z = 268.0 [(M+H)+].

The synthetic route of 3,5-Dibromochlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Blass, Benjamin E.; Iyer, Pravin; Abou-Gharbia, Magid; Childers, Wayne E.; Gordon, John C.; Ramanjulu, Mercy; Morton, George; Arumugam, Premkumar; Boruwa, Joshodeep; Ellingboe, John; Mitra, Sayan; Reddy Nimmareddy, Rajashekar; Paliwal, Shalini; Rajasekhar, Jamallamudi; Shivakumar, Savithiri; Srivastava, Pratima; Tangirala, Raghuram S.; Venkataramanaiah, Konda; Bobbala, Ramreddy; Yanamandra, Mahesh; Krishnakanth Reddy; Bioorganic and Medicinal Chemistry Letters; vol. 28; 13; (2018); p. 2270 – 2274;,
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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. 4152-90-3, name is (3-Chlorophenyl)methanamine, A new synthetic method of this compound is introduced below., name: (3-Chlorophenyl)methanamine

5-[3-(3-Chloro-benzylamino)-phenyl]-5-methyl-5,6-dihydro-2H-[l,4]oxazin-3-ylamine a) (RS)- (3-Chloro-benzyl)-[3-(5-methoxy-3-methyl-3,6-dihydro-2H-[l,4]oxazin-3-yl)- phenyl] -amineA dried pressure tube was charged consecutively under a nitrogen atmosphere with a solution of (RS)-3-(3-bromo-phenyl)-5-methoxy-3-methyl-3,6-dihydro-2H [l,4]oxazine (150 mg, 0.5 mmol) in toluene (5 ml), sodium tert-butylate (157 mg, 1.6 mmol), 2-di-tert-butylphosphino-2′,4′,6′- triisopropylbiphenyl (ie/t-butyl-x-phos) (23 mg, 0.1 mmol), tris(dibenzylideneacetone)- dipalladium chloroform complex (17 mg), and 3-chlorobenzylamine (154 mg, 1.1 mmol). The sealed pressure tube was heated at 100 C for 15 hours. After cooling, the reaction mixture was evaporated to dryness and directly purified by chromatography on an Isolute flash NH2 column using a gradient of heptane/ethyl acetate = 100/0 to 50/50 as the eluent. 85 mg (47%) of (RS)- (3-chloro-benzyl)-[3-(5-methoxy-3-methyl-3,6-dihydro-2H-[l,4]oxazin-3-yl)-phenyl]-amine were obtained as a yellow oil. Mass (calculated) C19H21CIN2O2 [344.844]; (found) [M+H]+ = 345.

The synthetic route of 4152-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A; ANDREINI, Matteo; GABELLIERI, Emanuele; GUBA, Wolfgang; HILPERT, Hans; MAUSER, Harald; MAYWEG, Alexander V.; NARQUIZIAN, Robert; POWER, Eoin; TRAVAGLI, Massimiliano; WOLTERING, Thomas; WOSTL, Wolfgang; WO2012/98064; (2012); A1;,
Chloride – Wikipedia,
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Application of 27139-97-5, 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.

To a reaction vessel purged with nitrogen were charged 45 g of 2-bromo-4-chlorotoluene, 36.6 g of carbazole, 7.0 g of a copper powder, 90.8 g of potassium carbonate, 4.7 ml of dimethyl sulfoxide, and 25 ml of dodecylbenzene, followed by heating, and stirred at 200°C for 44 hours. After cooling to 80°C, thereto was added 400 ml of toluene, an insoluble matter was removed by filtration therefrom, and vacuum concentration was conducted to obtain a crude product. Hexane was added to the crude product to precipitate the crude product. It was collected by filtration and then purified by column chromatography (carrier: silica gel, eluent: hexane) to obtain 20.3 g (yield: 32percent) of 9-(3-chloro-6-methylphenyl)-9H-carbazole as a white powder.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-4-chloro-1-methylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hodogaya Chemical Co., Ltd.; Shinshu University; YOKOYAMA Norimasa; KABASAWA Naoaki; ICHIKAWA Musubu; OTSURU Sohei; EP2679587; (2014); A1;,
Chloride – Wikipedia,
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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. 33050-38-3, name is 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine, A new synthetic method of this compound is introduced below., Quality Control of 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine

To a suspension of 3,6-dichloro-[1,2,4]triazolo[4,3-b]pyridazine (0.5 g, 1.8 mmol), 4-fluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide (0.8 g, 2.2 mmol) and Pd(dppf)Cl2.CH2Cl2 (0.15 g, 0.18 mmol) in DME (20 mL) was added a solution of Cs2CO3 (1.2 g, 3.6 mmol) in H2O (2 mL). The resulted mixture was stirred at 70 C. under N2 atmosphere for 12 hours and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=1/2) to give the title compound as a pale yellow solid (0.5 g, 64%). MS (ESI, pos. ion) m/z: 435.0 [M+H]+; 1H NMR (400 MHz, CDCl3): delta 10.20 (s, 1H), 8.71 (d, J=2.2 Hz, 1H), 8.46 (d, J=9.8 Hz, 1H), 8.27 (d, J=2.2 Hz, 1H), 8.04 (d, J=9.8 Hz, 1H), 7.90-7.87 (m, 2H), 7.42-7.38 (m, 2H), 3.79 (s, 3H).

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; Calitor Sciences, LLC; Xi, Ning; US2014/134133; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 63624-28-2, These common heterocyclic compound, 63624-28-2, name is 2,4-Dimethoxybenzene-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.

D) (2S, 4R)-1-[5-Chloro-1-(2,4-dimethoxyphenylsulfonyl)-3-(2,4-dimethoxypyrimidin-5-yl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-hydroxypyrrolidine-2-carboxylic acid dimethylamide Sodium hydride (12 mg of 60% dispersion in mineral oil, 0.3 mmol) was added to an ice-cold solution of the mixture of diastereomers from step C (139 mg, 0.30 mmol) in DMF (1.5 ml). The reaction mixture was stirred at 0 C. for 0.5 h and then 2,4-dimethoxyphenylsulfonyl chloride (71 mg, 0.3 mmol) was added. After the reaction mixture had been stirred at room temperature for one hour, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over magnesium sulfate. Purification by chromatography (silica gel, 5% MeOH in dichloromethane) resulted in 63 mg of the less polar diastereomer ((-) isomer) and 25 mg of the more polar diastereomer ((+) isomer) as colorless waxes.

The synthetic route of 63624-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbott GmbH & Co. KG; US2005/70718; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 2106-02-7, name is 2-Chloro-4-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 2106-02-7

Step A: Into a 20-L 4-neck round flask was placed a solution of 2-chloro-4- fluorobenzenamine (1300 g, 8.82 mol, 1.00 equiv, 99%) in toluene (10 L), 4- methylbenzenesulfonic acid (3.1 g, 17.84 mmol, 99%), and hexane-2,5-dione (1222.5 g, 10.62 mol, 1.20 equiv, 99%). The resulting solution was heated to reflux for 1 h in an oil bath and cooled. The pH value of the solution was adjusted to 8 with sodium carbonate (1 mol/L). The resulting mixture was washed with 1×5000 mL of water and concentrated under vacuum. The crude product was purified by distillation and the fraction was collected at 140 0C to afford l-(2- chloro-4-fluorophenyl)-2,5-dimethyl-lH-pyrrole (1700 g, yield: 85%).

The synthetic route of 2106-02-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; MATHIEU, Simon; PULK, Rebecca; RUDOLPH, Joachim; WEN, Zhaoyang; WO2011/25965; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, 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. COA of Formula: C7H7ClFN

General procedure: To a solution of bis(carboxymethyl)trithiocarbonate (0.22 mmol) in DME (1.0 mL) were added TEA (0.22 mmol) andthe opportune amine (0.22 mmol). The reaction mixture was heated at 90C for 10 min undermicrowave irradiation. After this time, the aldehyde 6 (0.22 mmol) was added, and the mixturewas heated at 110C for 5 min under microwave irradiation. The reaction mixture was evaporatedto dryness and the residue was additioned with MeOH and a drop of HCl 2N; the finalrhodanine derivatives were obtained as a pure precipitate, isolated by filtration, washed withwater and hexane, and finally dried under high vacuum. (Z)-4-(5-((3-(4-fluorophenethyl)-4-oxo-2-thioxothiazolidin-5-ylidene)methyl)furan-2-yl)-2-hydroxybenzoic acid (9a). (yield: 30%); Yellow solid. Mp = 292C (decomposition),

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

Reference:
Article; Tintori, Cristina; Iovenitti, Giulia; Ceresola, Elisa Rita; Ferrarese, Roberto; Zamperini, Claudio; Brai, Annalaura; Poli, Giulio; Dreassi, Elena; Cagno, Valeria; Lembo, David; Canducci, Filippo; Botta, Maurizio; PLoS ONE; vol. 13; 6; (2018);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7149-75-9, name is 4-Chloro-3-methylaniline, 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 7149-75-9, Product Details of 7149-75-9

A solution of (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert- butoxy)-4-oxobutanoic acid (10 g, 24.30 mmol) and 4-chloro-3-methylaniline (5.16 g, 36.5 mmol) in DCM (150 mL) at 0 °C was treated with DIEA (16.93 ml, 97 mmol) and cooled to °C. After 10 min, HATU (18.48 g, 48.6 mmol) was added portionwise. The reaction mixture was stirred at 0 °C for 1 h and the reaction mixture was partitioned between EA (50 mL) and an aqueous 1 M HCl solution (200 mL). The layers were separated and the organic layer was re-washed with an aqueous 1 M HCl solution (2 x 200 mL) and brine (200 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to 18.7 g (101percent) of Intermediate 17A as a beige solid. LCMS [m/z] calculated for C30H31ClN2O5: 534.2; found 557.2 [M+Na]+, tR=3.01 min (Method 4).1H NMR (400 MHz, DMSO- d6) delta 10.17 (s, 1H), 7.98? 7.78 (m, 3H), 7.78? 7.57 (m, 3H), 7.57? 7.29 (m, 6H), 4.50 (td, J = 8.4, 5.9 Hz, 1H), 4.43? 4.15 (m, 3H), 2.71 (dd, J = 15.9, 5.9 Hz, 1H), 2.55 (dd, J = 16.0, 8.7 Hz, 1H), 2.29 (s, 3H), 1.37 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-3-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; CELGENE INTERNATIONAL II SARL; YEAGER, Adam; TURNBULL, Philip; ZHANG, Lin; FAN, Junhua; TAMIYA, Junko; STEINBERG, Marcos; FOWLER, Tom; BENELKEBIR, Hanae; PASCERI, Raffaele; IEVA, Maria; GRANT, Kevan; TRAN, Yang; (403 pag.)WO2018/45246; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 60811-21-4, A common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, 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.

EXAMPLE 76 5′-(3-Chloro-4fluorophenyl)-spiro [cyclopentane-1,3′-[3H]indol]-2′(1’H)-one A solution of 3-chloro-4-fluoro-bromobenzene (0.4 cm3, 0.66 g, 3.1 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 cm3) was stirred under N2 for 20 minutes. To this mixture was then added (spiro[cyclopentane-1,3′-[3H]indol]-2′(1’H)-one-5-yl)boronic acid (1.0 g, 4.7 mmol) and sodium carbonate (1.0 g, 9.4 mmol) in water (5 cm3). The solution was brought to reflux for 18 hours and then cooled to room temperature, poured into 2N NaOH and extracted with EtOAc (*3). The combined extracts were washed with water, brine, dried (MgSO4), and evaporated. The residue was purified by column chromatography (SiO2, EtOAc, hexane) to afford the title compound (0.65 g, 66%) as a pale-yellow solid. mp: 202-204 C., 1H NMR (DMSO-d6) delta 10.4 (s, 1H), 7.9 (dd, 1H, J=2.3, 4.9 Hz), 7.7-7.6 (m, 1H), 7.6 (d, 1H, J=1.5 Hz), 7.5 (s, 1H), 7.4 (d, 1H, J=1.8 Hz), 6.9 (d, 1H, J=8.0 Hz), 2.0-1.9 (m, 8H); MS [M-H]-=314.

The synthetic route of 60811-21-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; Ligand Pharmaceuticals, Inc.; US6462032; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics