Author: Jessica.F

Electric Literature of 445-01-2,Some common heterocyclic compound, 445-01-2, name is 4-Bromo-1-chloro-2-(trifluoromethyl)benzene, molecular formula is C7H3BrClF3, 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.

PREPARATION 4 1-Benzyl-4-(4-chloro-3-trifluoromethyl-phenyl)-piperidine-4-ol (Prepared according to Collection Czechoslav. Chem. Commun. 1973, 38, 3879) A solution of 5-Bromo-2-chlorobenzotrifluoride (5 g, 19.2 mmol) in dry diethyl ether (40 ml) was added dropwise at room temperature to a mixture of Mg (470 mg) in dry diethyl ether (20 ml) under a stream of Argon (g). The reaction gave rise to a solution of Grignard’s reagent. A solution of 1-benzyl-4-piperidone (1.3 g, 6.88 mmol) in dry diethyl ether (30 ml) was added dropwise via syringe at room temperature. The combined mixture was stirred for 1 hour, and finally quenched with saturated ammonium chloride solution (40 ml). The mixture was extracted several times with EtOAc and the combined organic phases were dried (MgSO4), filtered and evaporated to dryness. The oily residue was chromathographed on a silica column using EtOAc:toluene (1:1 (v/v)) as eluent affording the title compound (1.6 g, 64%). MS m/z (relative intensity, 70 eV) 369 (M+, 23), 278 (15), 91 (bp), 65 (16), 56 (21).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-chloro-2-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; Sonesson, Clas; Andersson, Bengt; Waters, Susanna; Waters, Nicholas; Tedroff, Joakim; US2003/4169; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 90390-33-3,Some common heterocyclic compound, 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, molecular formula is C7H7ClFN, 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.

3.2 1 -l3enzyl-3-hydroxypyrrolidine-3-carboxylic acid (100mg) and 3-chloro-5-fluorobenzylamine (79 mg) are dissolved in one millilitre of dried DM50 and cooled to 0C. o-(7-Azabenzotrial-l -yl)-N,N,N?,N?-tetramethyluroniumhexafluorophosphate (206 mg) and 4-methylmorpholine (0.124 ml) are then added. The batch is stirred at 25 C. for 2 hours and then immediately purified by chromatography, giving N-(3-chloro-5-fluorobenzyl)-l -benzyl-3-hydroxypyrro- lidine-3-carboxamide (37 mg) as colourless amorphous solid.

The synthetic route of 90390-33-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GmbH; Heinrich, Timo; Zenke, Frank; Krier, Mireille; Friese-Hamim, Manja; Seenisamy, Jeyaprakashnarayanan; US2015/31670; (2015); 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. 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, A new synthetic method of this compound is introduced below., Computed Properties of C7H7ClFN

The compound of intermediate 2 (122 mg, 535 mumomicronIota) was provided in DMF (1.5 mL). N,N-diisopropylethylamine (280 mu, 1.6 mmol), propane phosphonic acid anhydride (T3P, 470 mu, 50% in DMF, 800 mumomicronIota) and 1-(3-chloro-5-fluorophenyl)methanamine (128 mg, 802 mumomicronIota) were added, and the mixture was stirred at room temperature for 4 days. After concentration, the remaining material was triturated with ethanol and water and the mixture was stirred for 15 minutes. The precipitate was collected by filtration, and was dried under reduced pressure. 156 mg (76% of theory) of the title compound were obtained. LC-MS (method 2): Rt = 1.12 min; MS (ESIpos): m/z = 370 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 2.323 (0.77), 2.327 (1.12), 2.332 (0.77), 2.523 (2.87), 2.665 (0.83), 2.669 (1.10), 2.674 (0.79), 2.729 (1.58), 2.889 (2.01), 4.481 (9.75), 4.496 (9.57), 7.167 (2.39), 7.174 (3.41), 7.177 (2.74), 7.191 (2.58), 7.195 (3.49), 7.198 (3.56), 7.201 (3.44), 7.205 (1.69), 7.219 (5.21), 7.224 (8.57), 7.233 (8.41), 7.242 (9.14), 7.247 (5.78), 7.260 (2.05), 7.272 (4.61), 7.277 (8.15), 7.280 (5.04), 7.313 (2.86), 7.318 (4.09), 7.324 (2.31), 7.335 (2.91), 7.341 (4.03), 7.346 (2.29), 7.457 (0.65), 7.466 (4.06), 7.470 (3.35), 7.476 (2.58), 7.483 (3.11), 7.489 (3.27), 7.500 (0.48), 7.597 (0.57), 7.607 (3.75), 7.613 (3.15), 7.620 (2.44), 7.626 (2.94), 7.630 (3.32), 7.638 (0.53), 7.823 (0.57), 8.306 (16.00), 8.986 (2.34), 9.001 (4.83), 9.015 (2.25), 9.138 (15.50), 13.287 (5.95).

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 PHARMA AKTIENGESELLSCHAFT; THEDE, Kai; ZORN, Ludwig; STEIGEMANN, Patrick; GRUeNEWALD, Sylvia; ALGIRE, Carolyn; NEUHAUS, Roland; CHRISTIAN, Sven; GUeNTHER, Judith; KOPPITZ, Marcus; SCHWEDE, Wolfgang; (78 pag.)WO2016/202756; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 33050-36-1, 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. 33050-36-1 name is 3-Chloro-[1,2,4]triazolo[4,3-b]pyridazine, 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.

3-Mercapto-s-triazolo[4,3-b]pyridazine A mixture of 1.20 g. (8 mmole) of 3-chloro-s-triazolo[4,3-b]pyridazine [P. Francavilla and F. Lauvia, J. Het. Chem., 8, 415 (1971) and 120 g. (16 mmole) of KSH in 20 ml. of ethanol was heated for 8 hours at 130 in a sealed tube. After cooling the mixture was evaporated to dryness and the residue was dissolved in 100 ml. of water, treated with active carbon, acidified to pH 1 with dil. HCl to precipitate 3-mercapto-s-triazolo[4,3-b]pyridazine which was collected, washed with 10 ml. of water and dried in vacuo over P2 O5 to yield 0.75 g. (62%), m.p. 260-270 (dec.). IR: nu maxKBr 3080, 2940, 2760, 1620, 1500, 1280, 1055 cm-1. NMR: ? ppmDMSO-d6 6.99 (1 H, d-d, 4 & 10 Hz, 7-H), 7.67 (1 H, d-d, 2 & 10 Hz, 8-H), 8.15 (1 H, d-d, 2 & 4 Hz, 6-H), 12.3 (1 H, br-s, disappear by addition of D2 O). Anal. Calcd. for C5 H4 N4 S. 1/2H2 O: C, 37.26; H, 3.13; N, 34.76. Found: C, 37.35; H, 2.32; N, 34.81.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-[1,2,4]triazolo[4,3-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Company; US3946000; (1976); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 121-27-7, name is 5-Chloro-2-(4-chlorophenoxy)aniline, 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 121-27-7, Formula: C12H9Cl2NO

EXAMPLE IV-3 STR526 A solution of 27.6 g (0.4 mol) of sodium nitrite in 31.7 ml of water is added dropwise with stirring at 0 C. to 5 C. to 84.3 g (0.3 mol) of 5-chloro-2-(4-chlorophenoxy)aniline (compare, for example, EP No. 34,771), 284 ml of water and 72.2 ml of concentrated hydrochloric acid, the mixture is stirred for a further 15 minutes after completion of the addition and filtered, 16.4 g (0.2 mol) of sodium acetate are added to the filtrate and the solution thus obtainable is added dropwise with stirring at 10 C. to 15 C. to a mixture of 253 ml of water, 123 g (1.5 mol) of sodium acetate, 2.5 g (0.015 mol) of sodium sulphate, 15.9 g (0.1 mol) of copper(II) sulphate and 28.3 g (0.48 mol) of acetaldoxime. After completion of the addition, the mixture is stirred for one hour at room temperature, the pH is then adjusted to 7 by addition of about 40 ml of concentrated hydrochloric acid, 292 ml of concentrated hydrochloric acid are then added in portions and the mixture is heated to reflux temperature for 3 hours. The reaction mixture is subjected to a steam distillation, the oil which separates is taken up in dichloromethane, and the solution is dried over sodium sulphate, concentrated and distilled in a high vacuum. 29.5 g (35% of theory) of 5-chloro-2-(4-chlorophenoxy)acetophenone of boiling point 80-85 C. at 1.5 mbar are obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-2-(4-chlorophenoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Aktiengesellschaft; US4956370; (1990); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 29027-17-6, The chemical industry reduces the impact on the environment during synthesis 29027-17-6, name is 2-Chloro-3-methylaniline, I believe this compound will play a more active role in future production and life.

a (2-Chloro-3-methyl-phenyl)-hydrazine The title compound was prepared in accordance with the general method of example 25a) from 2-chloro-3-methylaniline.

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-3-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bentley, Jonathan M.; Hebeisen, Paul; Muller, Marc; Richter, Hans; Roever, Stephan; US2002/35110; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 121-27-7, These common heterocyclic compound, 121-27-7, name is 5-Chloro-2-(4-chlorophenoxy)aniline, 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 43.6 g. of isonicotinic acid, 200 ml. of thionyl chloride and 200 ml. of methylene chloride is heated under reflux for 2 hours. The solvent is evaporated, 93.4 g. of 5-chloro-2-(p-chlorophenoxy)aniline, 180.0 g. of anhydrous potassium carbonate and 2800 ml. of benzene are added and the reaction proceeds as described in Example 1. Extraction with petroleum ether gives 5′-chloro-2′-(p-chlorophenoxy)-isonicotinanilide.

The synthetic route of 121-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US4221714; (1980); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 179897-90-6,Some common heterocyclic compound, 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, molecular formula is C6H2Br2ClF, 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.

To a round bottom flask under nitrogen fitted with a stir bar was added 1- chloro-2,6-dibromo-4-fluorobenzene (14.36 g, 49.8 mmol), pivalamide (5.04 g, 49.8 mmol), cesium carbonate (21.09 g, 64.7 mmol) and dioxane (250 mL). The reaction mixture was sparged with nitrogen and Pd(dba)2 (1.43 g, 2.490 mmol) and 5-bis(diphenylphosphino)-9,9- dimethylxanthene (XANTPHOS, 2.02 g, 3.49 mmol) were added. The reaction was then sealed and heated in an oil bath at 70 C for 18 h. The reaction was allowed to cool to r.t and was partitioned between a saturated aqueous solution of NH4C1 and EtOAc. The layers were separated and the aqueous portion was extracted with EtOAc (2 X). The combined organic portions were washed with water, brine, dried (Na2S04), filtered, concentrated, and adsorbed onto silica gel. Purification by flash chromatography on silica gel using an EtO Ac- heptane (1-20%) elution gradient afforded N- (3-bromo-2-chloro-5-fluorphenyl)pivalamide (1 1.0 g, 33.8 mmol, 68 %) as a white crystalline solid. LCMS (m/z): 309.9 (MH+), tR = 1.1 1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-2-chloro-5-fluorobenzene, its application will become more common.

Reference:
Patent; NOVARTIS AG; MADERA, Ann Marie; POON, Daniel; SMITH, Aaron; WO2011/161216; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 41332-02-9,Some common heterocyclic compound, 41332-02-9, name is 1-(2-Chloroethyl)naphthalene, molecular formula is C12H11Cl, 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: An aqueous solution of [18F]F- (0.5-3.5 mL, flow rate 0.5-30 mL/min) was passed through the column (borosilicate glass tubing, ID 4 mm, OD 0.6 cm, length 12 cm) packed with the resin (5-500 mumol; glass beads to fill the remaining volume). To remove the bulk of water, the column was flushed with He(gas) (flow rate 100 mL/min, 3 min). The column was dried by passing MeCN oracetone (1-10 mL, flow rate 1.5-20 mL/min) through, followed by a helium flush (100 mL/min,2-5 min). The column was primed by passing the radiofluorination solvent (MeCN for mannosetriflate, MeCN/tBuOH 1:5 for FLT-ONs, toluene for the naphthalene derivatives and 2-nitro-3-methoxypyridine, dry, 4 mL, flow rate 2 mL/min) through the column at room temperature followed by the substrate (50-100 mumol) dissolved in the radiofluorination solvent (dry, 3 mL) at 60-120 C (flow rate 0.55 mL/min). The radiofluorination solvent (dry, 2 mL, flow rate 0.55 mL/min) was then passed through the column again to elute the remaining product. The reaction mixture was analyzed by radio-TLC (eluent heptane:EtOAc 80:20 for the naphthalene derivatives, MeCN:H2O 95:5 for FDG, DCM:MeOH 9:1 for hydrolyzed FLT, petroleum ether:EtOAc 3:1 for the pyridine derivative. Total timeof radiosynthesis was 35-45 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(2-Chloroethyl)naphthalene, its application will become more common.

Reference:
Article; Mathiessen, Bente; Zhuravlev, Fedor; Molecules; vol. 18; 9; (2013); p. 10531 – 10547;,
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. 54773-20-5, name is 1,3-Dichloro-5-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Quality Control of 1,3-Dichloro-5-(trifluoromethyl)benzene

PREPARATION 1 1-(3-Chloro-5-trifluoromethyl-phenyl)-piperazine Beginning with 3,5-dichlorobenzotrifluoride (500 mg, 2.32 mmol) and piperazine (1 g, 11.6 mmol), 320 mg of the title compound was recovered by the procedure described in Example-1.

The synthetic route of 54773-20-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sonesson, Clas; Andersson, Bengt; Waters, Susanna; Waters, Nicholas; Tedroff, Joakim; US2003/4169; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics