Author: Jessica.F

Synthetic Route of 1000572-88-2, 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. 1000572-88-2 name is 2,5-Dibromo-1-chloro-3-fluorobenzene, 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.

An autoclave equipped with a stir bar was charged with 2,5-dibromo- l-chloro-3-fluorobenzene (5.0 g, 17.3 mmol), triethylamine (12.1 mL, 86.7 mmol), bis(diphenylphosphino)ferrocene)palladium(II) Chloride (0.86 mmol, 708 mg) and methanol (100 mL) was degassed with nitrogen for 10 min. Then the container was sealed and filled with CO to 400 psi. The reaction mixture was heated at 100 C with stirring for 12 hours. The reaction mixture was filtered through Celite, washed with MeOH, and the filtrate was concentrated. The crude product was purified by silica gel chromatography (0-10% EtOAc/hexane) to afford the title compound as a colorless oil which solidified in high vacuum (3.06 g, 71% yield). ¾ NMR (400 MHz, CDC13) delta 7.90 (s, 1H), 7.69 (dd, J = 9.0, 1.2 Hz, 1H), 3.99 (s, 3H), 3.95 (s, 3H). LCMS (APCI+) 247.0[M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,5-Dibromo-1-chloro-3-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); 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. 2729-36-4, name is 4,5-Dichloro-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H4Cl2FN

In brief, 3,4-Dicliloro-6-fluoroaniline (1 equivalent, prepared as described in U.S. Patent No. 6,126,917) was reacted with 4-chloro-7-fluoro-6-nitroquinazoline (3.5 equivalents, Compound 24, prepared as described hereinabove), in a mixture of iso-propylalcohol/ dichloromethane. After filtration, 4,5-dichloro-2-fluoro-phenyl-(7-fluoro-6-nitro- quinazolin-4-yl)-amine was obtained.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2729-36-4.

Reference:
Patent; T.K. SIGNAL LTD.; WO2007/29251; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 327-76-4, name is 1-Chloro-2,4-bis(trifluoromethyl)benzene, 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 327-76-4, HPLC of Formula: C8H3ClF6

[0199] To a solution of 95 (25.0 g, 0.10 mol) in anhy. THF (150 mL) was added NaOCH3 (7.0 g, 0.13 mol) at 0C. The mixture was then heated at 50C for 6 h. After cooling to 25C, the reaction mixture was quenched with sat. NH4C1, diluted with EtOAc, washed with brine, and concentrated in vacuo to afford crude methyl ether 96 (17.93 g, 73%) as a colorless liquid. This product was sufficiently pure to be used directly in subsequent reaction. 1H NMR (400 MHz, CDC13) : 8 7.83 (1H, s), 7.77 (1H, d, J = 8. 4 Hz), 7.09 (1H, d, J= 8.4 Hz), 3.97 (3H, s) ppm. A solution of methyl ether 96 (9.98 g, 0.04 mol) in anhyrous CH2C12 (150 mL) was cooled to-78C and treated with BBr3 (6.0 mL, 0.063 mol). The resultant brown mixture was stirred for 1 h at-78C, and then warmed up to 25C over 4 h, and then quenched with water. The organic layer was separated and washed with sat. NaHCO3 and brine, dried over Na2S04, concentrated to-13 mL in vacuo below 0C and used directly in the following substitution reaction. Take this solution (ca. 1.15 mL) and diluted with DMF (8 mL), and then treated with K2CO3 (1.27 g) and bromide 79 (1.72 g). The resultant mixture was stirred at room temperature for 1 h, diluted with EtOAc, washed with water and brine, dried over Na2S04, and concentrated in vacuum. The residue was purified by flash chromatography (5: 95 EtOAc/hexanes) on silica gel and then recrystallized with 10 % EtOAc/hexanes to give pure ester 97 as a white solid. 1H NMR (400 MHz, DMSO-d6) : No. 8. 60 (1H, d, J= 2.2 Hz), 8.17 (1H, dd, J= 8.6, 2.2 Hz), 7.96 (1H, s), 7.91 (1H, d, J= 8.6 Hz), 7. 84 (1H, d, J= 8.2 Hz), 7.74 (1H, t, J= 7.8 Hz), 7.38 (1H, d, J= 9.0 Hz), 6.40 (1H, s), 4.19 (2H, m), 1.11 (3H, t, J = 7.2 Hz) ppm.

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; METABOLEX, INC.; WO2005/80340; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 697-88-1,Some common heterocyclic compound, 697-88-1, name is 4-Bromo-2,6-dichloroaniline, molecular formula is C6H4BrCl2N, 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.

Pd (OAc) 2 (186 mg), P (o-Tol) 3 (505 mg), Et3N (1.73 ml), 4-bromo-2,6- dichlorobenzeneamine (2.0 g) and acrylamide (885 mg) were dissolved in MECN (15 ml) and N2 was bubbled through the reaction mixture for at least 20 minutes. Then a cooler was mounted strictly under nitrogen atmosphere. The reaction mixture was heated at 70 C overnight. The reaction mixture was allowed to cool to 20 C and was diluted with CH2CI2 and washed with saturated aqueous NAHC03 (2x) and dried with brine and NA2SO4. The residue was sonicated in diisopropyl ether and filtered off. Yield: 0.55 g of intermediate 18 (30%).

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-2,6-dichloroaniline, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; ARTS, Theodora, Joanna, Francisca; JANSSEN, Graziella, Maria, Constantina; JANSSEN, Herwig, Josephus, Margareta; JANSSEN, Jasmine, Josee, Werner; JANSSEN, Paul, Peter, Maria; JANSSEN, Maroussia, Godelieve, Frank; WO2004/74266; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 167404-32-2, A common heterocyclic compound, 167404-32-2, name is 4-Cyclopropylbenzene-1-sulfonyl chloride, molecular formula is C9H9ClO2S, 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.

Compound 46. Crude compound 45 (13.3 g) was dissolved in 200 mL of acetone and 60 mL of water. Potassium fluoride (7.12 g, 122 mmol) was added and the reaction mixture was stirred overnight at rt. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was dried with Na2SO4, filtered, and concentrated to dryness to give 9.80 g (97%) of crude p-cyclopropyl benzenesulfonyl fluoride (Compound 46).

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; Schering Corporation; US2003/232859; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 320-50-3, The chemical industry reduces the impact on the environment during synthesis 320-50-3, name is 1,4-Dichloro-2-(trifluoromethyl)benzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 8 4-Chloro-2-trifluoromethylphenol To a 300 ml, 3-necked flask fitted with a stirrer, condenser, thermometer and drying tube is added dimethylsulfoxide (100 ml), tert-butanol (20 ml), powdered potassium hydroxide (KOH) pellets (85%, 30 g) and 2,5-dichlorobenzotrifluoride (21.5 g, 0.10 mole). The reaction mixture is warmed to 71-73 C. for 60 hours, then additional KOH (10 g) is added and heating is continued at 73-75 C. for 24 hours. The reaction mixture is cooled and the solvent partially removed by distillation at 0.9 mm, bp 55 C.). The cooled pot residue is then poured into ice water (1000 g) which had been preacidified to pH 1 with conc. HCl (50 ml). The aqueous mixture is extracted with carbon tetrachloride (CCl4), the CCl4 layer decanted and dried and the solvent removed under vacuum to afford 10.8 g of 4-chloro-2-trifluoromethylphenol, which is sublimed to afford pure product, mp 81-81.5 C. Elemental Anal. Calcd for C7 H4 ClF3 O: C, 42.75; H, 2.06; Cl, 18.04: Found: C, 42.54; H, 2.36; Cl, 18.16. STR14

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, 1,4-Dichloro-2-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rohm and Haas Company; US4259510; (1981); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 625-98-9, A common heterocyclic compound, 625-98-9, name is 1-Chloro-3-fluorobenzene, molecular formula is C6H4ClF, 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 solution of 261.1 g (2.0 mol) of 1-chloro-3-fluorobenzene in 2000 ml of dry tetrahydrofuran under nitrogen is cooled to -78. To the solution is added 960 ml (2.4 mol) of 2.5 M n-butyllithium in hexanes over a period of 40 minutes. After stirring for 2.5 hours, a slurry of 155 ml of bromine cooled to -78 is added over 30 minutes and the mixture is stirred for 40 minutes before warming to -10. The reaction is quenched with an aqueous solution of 151.3 g (1.2 mol) of sodium sulfite and 16.0 g (0.4 mol) of sodium hydroxide in 500 ml of water. The organic layer is separated, the solvents are removed at ambient pressure, and the product is distilled at 92-96 (20 mm Hg) to obtain 2-bromo-3-fluoro-chlorobenzene as a colorless oil.

The synthetic route of 625-98-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; US6291523; (2001); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 621-62-5, A common heterocyclic compound, 621-62-5, name is 2-Chloro-1,1-diethoxyethane, molecular formula is C6H13ClO2, 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 2 Preparation of 2-benzoyloxyacetaldehyde diethyl acetal Chloroacetaldehyde diethyl acetal (2.00 g), potassium benzoate (1.91 g), potassium iodide (0.41 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (30 mL) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration, the organic layer was separated, was subjected to vacuum concentration and then to Kugelrohr distillation at 110-120 C. and at 1 mmHg and thereby yielded the target compound (2.41 g) in a yield of 77%.

The synthetic route of 621-62-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daicel Chemical Industries, Ltd.; US2005/234246; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 454-78-4,Some common heterocyclic compound, 454-78-4, name is 2-Bromo-1-chloro-4-(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.

3-Bromo-4-chlorobenzotrifluoride and piperazine were dissolved in NMP (2 mL) and heated to 200C for 30 mins in a microwave reactor. NMP was removed using flash chromatography (1 :10 MeOH:DCM) to give 1-(2-bromo-4-(trifluoromethyl)phenyl) piperazine (RD71 ) which was used without further purification

The synthetic route of 454-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NATIONAL UNIVERSITY OF IRELAND, MAYNOOTH; STEPHENS, John; FINDLAY, John; KINSELLA, Gemma; MARTIN, Darren; DEVINE, Robert; VELASCO-TORRIJOS, Trinidad; WO2013/60860; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 909122-17-4, 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. 909122-17-4 name is 1-Bromo-2-chloro-4-ethoxy-3-fluorobenzene, 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.

First Step 1.0 g of well dried magnesium and 30 mL of THF were placed in a reactor under nitrogen atmosphere, and heated to 43° C. 10.0 g of 1-bromo-2-chloro-4-ethoxy-3-fluorobenzene (6) dissolved in 20 mL of THF was slowly added dropwise thereto at a temperature range of from 43 to 51° C., followed by stirring for 30 minutes. Thereafter, 21.2 g of 4-(2-(trans-4-propylcyclohexyl)ethyl)cyclohexanone (7) dissolved in 20 mL of THF was slowly added dropwise thereto at a temperature range of from 50 to 55° C., followed by stirring for 30 minutes. After cooling the resulting reaction mixture to 25° C., the reaction mixture was mixed with 100 mL of 3N hydrochloric acid and 100 mL of toluene in a vessel and separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with water, a 2N sodium hydroxide aqueous solution, a saturated sodium bicarbonate aqueous solution and water, followed by drying over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure to obtain 16.4 g of 1-(2-chloro-4-ethoxy-3-fluorophenyl)-4-(2-(trans-4-propylcyclohexyl)ethyl)cyclohexanol (8). The resulting compound (8) was a yellow solid matter.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-chloro-4-ethoxy-3-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Chisso Corporation; Chisso Petrochemical Corporation; US2008/75891; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics