Author: Jessica.F

Reference of 348-59-4, These common heterocyclic compound, 348-59-4, name is 2,5-Dichlorofluorobenzene, 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.

Intermediate 124 2,5-Dichloro-4-fluorobenzenesulfonyl chlorideA mixture of 1 ,4-dichloro-2-fluorobenzene (5 g, 30.3 mmol) and fuming sulfuric acid (18- 24% SO3, 20 ml) was heated at 1 10 0C overnight. After cooling down to room temperature, the reaction mixture was carefully poured into ice (700 g). The resulting mixture was stirred at room temperature for 30 min followed by addition of ethyl acetate. The aqueous layer was isolated and concentrated under vacuum. The precipitate was filtered off to give 2,5-dichloro-4-fluorobenzenesulfonic acid as white crystals (3.33 g, 45%).The acid previously prepared (2.0 g, 8.2 mmol) and phosphorus pentachloride (5 g, 24 mmol) were heated at 110 0C overnight. After cooling down to room temperature, the reaction mixture was carefully poured into ice (50 g) The resulting mixture was stirred at room temperature for 30 min followed by addition of ethyl acetate (100 ml_). The ethyl acetate layer was isolated and concentrated under vacuum to give the title compound as yellow oil (1.29 g, 60%). 1H NMR(d6-DMSO) delta 7.62 (d, 1 H), 7.95 (d, 1 H).

Statistics shows that 2,5-Dichlorofluorobenzene is playing an increasingly important role. we look forward to future research findings about 348-59-4.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/26197; (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 202197-26-0 as follows. Safety of 3-Chloro-4-((3-fluorobenzyl)oxy)aniline

To 2-propanol (300 mL) were sequentially added 4-chloro-5,8-dihydro-6H-spiro[l- benzothieno[2,3-d]pyrimidme-7,2′-[l,3]dioxolane] (20.7 g, 73.2 mmol), 3-Chloro-4-(3- fluoro-benzyloxy)-phenylamine (18.4 g, 73.2 mmol), and HCl in dioxane (4N, 0.92 mL). The suspension was stirred with heating to 80 0C, upon which the contents turn brown and homogeneous. After 15 h, the dark orange-yellow heterogeneous mixture was removed from heating, and allowed to cool to rt. The contents were filtered and the collected solid product dried under vacuum. The filtrate was concentrated under reduced pressure and the EPO residue suspended in CH3OH (50 niL), upon which formation of a second crop of product ensues. The second crop was collected, and from this filtrate a third crop could also be obtained. The solid product crops were combined to afford the final product (33.5 g, 92%) as an off-white solid. 1H-NMR delta 1.90 (t, 2H), 3.00 (s, 2H), 3.26 (t, 2H), 3.97 (s, 4H), 5.22 (s, 2H), 7.11-7.30 (m, 4H), 7.41-7.55 (m, 2H), 7.74 (s, IH), 8.33 (s, IH), 8.39 (s, IH); LCMS RT = 3.63 min; [M+H]+ = 498.3.

According to the analysis of related databases, 202197-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/55268; (2006); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2453-46-5, name is Chlorocycloheptane, 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 2453-46-5, name: Chlorocycloheptane

General procedure: A 10 mL Schlenk tube was charged with CoBr2 (6.6 mg, 0.03mmol), 1,3-diisopropyl-1H-benzimidazol-3-ium bromide (L4; 8.5mg, 0.03 mmol), 4-methoxy-N-[(1E)-1-phenylethylidene]aniline(1a, 67.6 mg, 0.30 mmol), 1-chlorooctane (2a, 76.5 muL, 0.45 mmol), and THF (0.69 mL). A 1.92 M solution of t-BuCH2MgBr inTHF (0.31 mL, 0.60 mmol) was added dropwise at 0 C, and themixture was stirred at r.t. for 6 h. The reaction was quenched by theaddition of 3 M aq HCl (1.0 mL), and the mixture was stirred at r.t.for 1 h, then extracted with EtOAc (3 × 10 mL). The organic layerswere combined, dried (MgSO4), and concentrated under reduced pressure. The crude product was purified by chromatography [silicagel, hexane-EtOAc (40:1)].

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:
Article; Gao, Ke; Yamakawa, Takeshi; Yoshikai, Naohiko; Synthesis; vol. 46; 15; (2014); p. 2024 – 2039;,
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. 445-13-6, name is 3-Chloro-4-(trifluoromethyl)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 445-13-6

Example 2 (variant b) STR11 0.5 mol of chloroformic acid phenyl ester is added to a solution of 0.5 mol of p-fluoroaniline in 300 ml of dichlorobenzene and 70 ml (0.5 mol) of triethylamine, whilst cooling (0-10 C.). The reaction mixture is then left to stand at room temperature for 24 hours. The triethylamine hydrochloride which has formed is filtered off and 0.5 mol of 3-chloro-4-trifluoromethylaniline is added to the filtrate. The reaction solution is heated to 180 C. for 6 hours, the solvent is stripped off in vacuo and the residue is boiled up in 250 ml of ether and filtered off again. N-4-Fluorophenyl-N’-3-chloro-4-trifluoromethylphenylurea of melting point 212 to 214 C. is obtained. Yield: 67% of theory.

The synthetic route of 445-13-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US4405644; (1983); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

886762-39-6, name is 3,4-Dichloro-2-fluoroaniline, 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. Product Details of 886762-39-6

Example 1 Preparation of 4-(3,4-dichloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yl acetate (the compound of formula (VI)) 7-methoxy-4-oxo-3,4-dihydroquinazolin-yl acetate (100 g) was added to toluene (850 ml) and N,N-diisopropylethylamine (82.5 ml). Phosphorusoxy chloride (100 ml) was added thereto over 20 minutes at 75 C., followed by stirring for 3 hours. Toluene (450 ml) and 3,4-dichloro-2-fluoroaniline (84.6 g) were added to the resulting mixture, followed by stirring for 2 hours. Upon completion of the reaction, the resulting mixture was cooled to 25 C. The solid thus obtained was filtered under a reduced pressure and washed with toluene (400 ml). Isopropanol (1,000 ml) was added to the solid, which was then stirred for 2 hours. The resulting solid was filtered and washed with isopropanol (400 ml). The solid was dried at 40 C. in an oven to produce the compound of formula (VI) (143 g, yield: 83%). 1H-NMR (DMSO-d6, 300 MHz, ppm) delta 8.92 (s, 1H), 8.76 (s, 1H), 7.69-7.57 (m, 3H), 4.01 (s, 3H), 2.38 (s, 3H).

The synthetic route of 886762-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bang, Keuk Chan; Moon, Young Ho; Chang, Young Kil; US2014/275534; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 694-80-4, name is 1-Bromo-2-chlorobenzene, 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 694-80-4, category: chlorides-buliding-blocks

Intermediate 86 2,2′-Dichloro-6-methoxy-biphenyl: To a solution of 2-chlorobromobenzene (15.5 g, 80.6 mmol) and sodium carbonate (9.0 g, 84.9 mmol) in DME-water (5:1) was added 2-chloro-6-methoxybenzene boronic acid (5.0 g, 26.8 mmol) at 82 C., followed by tetrakis(triphenylphosphine)palladium (0) (1.5 g, 1.4 mmol). The reaction mixture was heated at 82 C. overnight and cooled to room temperature. The mixture was extracted with ethyl acetate and washed with water. The organic solvent was removed under vacuum. Chromatography with 5% ethyl acetate in hexanes afforded 5.0 g (73%) of the title compound as a colorless oil.

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-Bromo-2-chlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wyeth; US2006/241172; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 118-69-4, 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. 118-69-4 name is 2,6-Dichlorotoluene, 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.

235.0 g (3.0 mol) of acetyl chloride were added dropwise with stirring at 100 C. in the course of 2 hours to a solution of 502.0 g (3.12 mol) of 2,6-dichlorotoluene and 408.0 g (3.06 mol) of aluminum trichloride. After the mixture had been stirred for 2 hours at 100-105 C. it was cooled, and the reaction mixture was poured onto 3 l of ice and 1 l of water. The solid which had precipitated during this process was filtered off with suction and washed to neutrality with 800 ml of water. After drying at 40 C., 500.0 g of 2,4-dichloro-3-methylacetophenone were obtained as crude product, which were subsequently distilled under a high vacuum. (Boiling point: 121-128 C. (4 mbar))

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichlorotoluene, and friends who are interested can also refer to it.

Reference:
Patent; BASF Aktiengesellschaft; US6028035; (2000); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

38762-41-3, name is 4-Bromo-2-chloroaniline, 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. COA of Formula: C6H5BrClN

[00219] Step C: 4-(4-Bromo-2-chlorophenylamino)-6-chloronicotinic acid:[00220] To a solution of 2-chloro-4-bromoaniline (6.776 g, 33.1 mmol) in 50 ml anhydrous THF was added LHMDS (50 ml, 50 mmol, 1M/THF) over a period of 15 min at -78 C. It was stirred for an additional 30 min., then a solution of 4,6-dichloronicotinic acid (3 g, 15.7 mmol) in 50 ml THF was added dropwise. After complete addition the mixture was gradually allowed to warm to room temperature and the reaction mixture was stirred for an additional 12 hours. The mixture was quenched with H2O and 1N HCl was added (pH 0-1) followed by brine. It was extracted using THF and dried with Na2SO4. The solvent was removed and the solid crude product was suspended in 200 ml EtOAc. The suspension was heated with stirring at the reflux temperature for 5 min. It was cooled to room temperature and the precipitate was filtered and washed with EtOAc and dried at 50 C for 5 h in oil pump vacuo to obtain the title compound as an off-white solid (4.05 g, 72%). Rf (CHCl3/MeOH 10:1 ) = 0.3. 1H-NMR (500 MHz, DMSO-D6): delta = 10.12 (s, 1H), 8.65 (s, 1H), 7.88 (s, 1H), 7.62-7.57 (dd, 1H), 7.55-7.48 (dd, 1H), 6.67 (s, 1H).

The synthetic route of 38762-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDEA BIOSCIENCES, INC.; WO2008/89459; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 4584-46-7, 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 4584-46-7 as follows.

Me2N(CH2)2Cl.HCl (1.77 g, 12 mmol), K2CO3(3.40 g, 25 mmol) and water (8 mL) were added to 31 (1.68 g, 8.2 mmol)in CHCl3 (40 mL). The stirred solution was placed in an oil bath at65C. The temperature was slowly raised to 80C during 65 min and themixture was stirred for 16 h at 80C. The organic phase was separated and thesolvent was evaporated to 25% of its original volume. This solution was combinedwith the aqueous phase and diluted with water and toluene. The organic layerwas separated, washed with water and extracted with aq. HCl (1.0 M). The acidicphase was washed (toluene), cooled to 0C, basified (~pH 12) by addition ofaq. NaOH (4.0 M) and extracted (toluene). The extract was washed (water,brine) and dried. Evaporation gave 32 (1.81 g, 80%) as a white solid: mp108-109 (lit.3 mp 110C); IR numax 3315, 1687; 1HNMR d 1.39 (3 H, t, J = 7.1 Hz, OCH2CH3), 2.35 (6 H, s, NMe2),2.76 (2 H, t, J = 5.8 Hz, Me2NCH2CH2), 4.10 (2 H, t, J = 5.8 Hz, Me2NCH2CH2),4.39 (2 H, q, J = 7.1 Hz, OCH2CH3),6.99 (1 H, dd, J = 8.9, 2.4 Hz, 6-H),7.07 (1 H, d, J = 2.4 Hz, 4-H), 7.12(1 H, dd, J = 2.1, 0.8 Hz, 3-H), 7.28(1 H, d, J = 8.9 Hz, 7-H), 9.30 (1 H,s, NH); 13C NMR d14.32 (OCH2CH3),45.83 (NMe2), 58.38 (Me2NCH2CH2), 60.82 (OCH2CH3), 66.57 (Me2NCH2CH2), 103.67 (4-C), 108.13(3-C), 112.69 (7-C), 117.37 (6-C), 127.74 (2-C), 127.89 (3a-C), 132.42 (7a-C),153.83 (5-C), 162.01 (C=O)

According to the analysis of related databases, 4584-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Twum, Elvis A.; Nathubhai, Amit; Wood, Pauline J.; Lloyd, Matthew D.; Thompson, Andrew S.; Threadgill, Michael D.; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3481 – 3489;,
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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

To a solution of 2-t-butoxycarbonylaminobenzoic acid (115 mg, 0.485 mmol) in DMF (2.0 mL) was added a solution of 4-chloro-3-methoxyaniline (82.2 mg, 0.522 mmol), HOBt (70.0 mg, 0.518 mmol), EDCI·HCl (104 mg, 0.542 mmol) and DIEA (90.0 muL, 0.522 mmol) in DMF (1.0 mL). The resulting mixture was stirred at r.t. overnight. After completion of the reaction, AcOEt was added. The organic layer was washed with water and brine, dried, and concentrated to give the title compound as a pale yellow paste, which was used for the next step without further purification.

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:
Article; Numadate, Akiyoshi; Mita, Yusuke; Matsumoto, Yotaro; Fujii, Shinya; Hashimoto, Yuichi; Chemical and Pharmaceutical Bulletin; vol. 62; 10; (2014); p. 979 – 988;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics