Tag: M.W=200-300

Some common heterocyclic compound, 60811-18-9, name is 4-Bromo-1-chloro-2-fluorobenzene, molecular formula is C6H3BrClF, 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. Computed Properties of C6H3BrClF

EXAMPLE 1 A mixture of 0.1 mole of 4′-n-propyl-4-biphenylboronic acid (obtained by the reaction of the Grignard reagent of 4′-n-propyl-4-bromobiphenyl and trimethyl borate), 0.1 mole of 4-chloro-3-fluorobromobenzene, tetrakis (triphenylphosphine) palladium (1 mole %), 2 m sodium carbonate solution (150 ml), toluene (250 ml) and IMS (60 ml) is stirred and refluxed for 16 hrs under a nitrogen atomosphere. After usual work-up 4-chloro-3-fluoro-4′-(p-n-propylphenyl) -biphenyl is obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 60811-18-9, its application will become more common.

Reference:
Patent; Merck Patent Gesellschaft mit beschrankter Haftung; US5482653; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 16793-91-2, name is 2-Chlorophenethyl Bromide, 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. Quality Control of 2-Chlorophenethyl Bromide

EXAMPLE 1 Preparation of 1-(2-chlorophenyl)-3-(4-pyridyl)-butane In a 200-ml flask, 0.94g (9.35 mmol) of diisopropyl amine and 15 ml of tetrahydrofuran were placed and cooled to -50 C. Then 6.5 ml (10.3 mmol) of n-butyl lithium (15% n-hexane solution) was added thereto under nitrogen atmosphere. The resulting mixture was stirred for 10 minutes, and a solution of 1.0 g (9.35 mmol) of 4-ethylpyridine dissolved in tetrahydrofuran was added dropwise. After stirring for 30 minutes at -50 C., the reaction temperature was gradually raised up to -10 C., which was kept for 30 minutes, and lowered again to -50 C. A solution of 2.05 g (9.35 mmol) of 2-chlorophenethyl bromide dissolved in tetrahydrofuran was added dropwise to the reaction mixture, and after stirring for 30 minutes at -50 C., the temperature was raised up to room temperature. Subsequently, water was added, tetrahydrofuran was distilled away under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, then dried over anhydrous sodium sulfate. Then, the solvent was distilled away under reduced pressure, to obtain an oil. Said oil was purified by silica gel column chromatography, to obtain 1.35 g of the desired compound (yield: 58.2%). The resulting compound was identified as 1-(2-chlorophenyl)-3-(4-pyridyl)-butane (hereinafter referred to as compound 1) by melting point, infrared ray absorption spectrum (IR), nuclear magnetic resonance spectrum (NMR) and elementary analysis.

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

Reference:
Patent; Idemitsu Kosan Co., Ltd.; US5262420; (1993); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 41965-95-1, 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. 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2 (1.92 mmol), 3-chloro-4-methoxybenzylamine hydrochloride (2.11 mmol), NaI (0.1 mmol), and phenol (3.84 mmol) was heated at 130 C. for 1.5 h. After cooling the reaction down, Et2O (20 mL) was added and washed with 1N NaOH (3¡Á20 mL). The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by Flash Chromatography (AcOEt:MeOH 8:2) to give the desired compound A (38% yield). 1H NMR (300 MHz, CDCl3) delta 8.04 (d, 1H, J=2.1 Hz), 7.80 (d, 1H, J=8.7 Hz), 7.64 (dd, 1H, J1=2.1, J2=9.0 Hz), 7.38 (d, 1H, J=2.1 Hz), 7.16 (dd, 1H, J1=2.1, J2=8.4 Hz), 6.91 (d, 1H, J=8.4 Hz), 4.47 (d, 2H, J=5.7 Hz), 3.91 (s, 3H), 3.54 (s, 2H), 3.18 (t, 2H, J=6.3 Hz), 2.81 (t, 2H, J=6.3 Hz), 2.50 (s, 3H).

The synthetic route of 3-Chloro-4-methoxybenzylamine Hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; Landry, Donald W.; Deng, Shixian; Arancio, Ottavio; Fiorito, Jole; Wasmuth, Andrew; (41 pag.)US10626113; (2020); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 60811-21-4,Some common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, molecular formula is C6H3BrClF, 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.

Step 1: tert-Butyl 4-(3-chloro-4-fluorophenyl)piperazine-1-carboxylate A solution of tert-butyl-piperazine-1-carboxylate (1.0 g, 5.37 mmol), 4-bromo-2-chloro-1-fluorobenzene (1.35 g, 6.44 mmol), t-BuONa (768 mg, 8.06 mmol), BINAP (125 mg, 0.2 mmol), Pd2(dba)3 (92 mg, 0.1 mmol) in dry toluene (10 mL) was stirred under N2 at 80 C. for 16 hrs. The reaction mixture was concentrated and the mixture was purified by chromatography (silica, EtOAc/PE=1/10) to afford tert-butyl-4-(3-chloro-4-fluorophenyl)piperazine-1-carboxylate (1.3 g, 4.13 mmol, 77%) as a yellow oil. ESI-MS (EI+, m/z): 259 [M-55]+.

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-chloro-1-fluorobenzene, its application will become more common.

Reference:
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (136 pag.)US2019/389843; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 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. SDS of cas: 202197-26-0

Step A: preparation of 4-[3-chloro-4-(3-fluoro-benzyloxy)phenylamino]-6-nitroquinazoline 1.20 g (5.7 mmol) of 4-chloro-6-nitro-quinazoline (prepared by referring to) and 1.37 g (5.6 mmol) of 4-(3-fluoro-benzyloxy)-3-chloro-aniline (prepared by referring to) were dissolved in 80mL of isopropanol and refluxed for 3 hours. A large amount of yellow solid was precipitated from the system, and was filtered. The filter cake was washed with a saturated sodium bicarbonate solution till pH=8 and dried under vacuum to obtain 1.62g (3.75 mmol) of yellow solid, which was identified as the compound 4-[3-chloro-4-(3-fluoro-benzyloxy)phenylamino]-6-nitro-quinazoline with a yield of 67%. 1H-NMR(400MHz, CDCl3): delta11.30(1H, br), 9.54-9.48(1H, m), 8.45-8.41(1H, m), 8.31-8.25(1H, m), 7.98-7.89(1H, m), 7.50-7.47(1H, m), 7.35-7.26 (1H, m), 7.05-6.96(1H, m), 6.90-6.80(2H, m), 7.74-7.60(2H, m), 4.84(2H, s).

The synthetic route of 202197-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Allist Pharmaceutical., Inc.; EP2269994; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 699-89-8, 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. 699-89-8, name is 4,7-Dichlorothieno[2,3-d]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Equal equivalents of dichloride (1) and M-NH2 are refluxed in the appropriate amount of absolute ethanol at 95 C. for 2 hrs. The reaction mixture is allowed to cool to room temperature and the precipitate (2) that forms is filtered and washed sequentially with isopropyl alcohol, 4.0 N KOH, H2O, and hexane, and then dried. The filtrate (2) is then reacted with 1.2 equivalent of Q-NH2 in an appropriate amount of n-butyl alcohol at 150 C. for 10 hrs. The reaction is cooled to room temperature before the solvent is evaporated under reduced pressure. The residue is treated with aqueous 4.0 N KOH solution and extracted with dichloromethane. The organic layer is dried (MgSO4) and evaporated. The crude product (3) is purified by preparative thin layer chromatography (TLC) or flash chromatography on silica gel using dichloromethane/methanol (95:5) as the eluent. Final product is confirmed by LC/MS and/or NMR. The invention compounds of Examples 23-25, 48, and 76-80 as shown in the below table were prepared by method A-1.

The synthetic route of 4,7-Dichlorothieno[2,3-d]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharmaceuticals Corporation; US6689883; (2004); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application 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.

N-(6-chloro-5-cyanopyridin-3-yl)-3,5-difluorobenzene-sulfonamide 1.132 g (5.32 mmol) of 3,5-difluorobenzene-1-sulfonyle chloride is added under argon to a solution of 545 mg (3.55 mmol) of 5-amino-2-chloronicotinotrile in 20 mL of an anhydrous 1:1 mixture of THF and pyridine. The reaction medium is heated to 70 C. for 3 hours and let 12 additional hours under stirring at room temperature. The solvent is dry evaporated and the crude reaction product is redissolved in ethyl acetate and washed with several aqueous fractions. The organic phase is dried on magnesium sulfate, filtered, concentrated and then purified by silica gel chromatography to yield 784 mg (67%) of N-(6-chloro-5-cyanopyridin-3-yl)-3,5-difluorobenzene-sulfonamide. 1H NMR: deltaH ppm (400 MHz, DMSO): 11.39 (1H, s1, NH), 8. 34 (1H, m, CHarom), 8.10 (1H, m, CHarom), 7.67 (1H, m, CHarom), 7.59 (2H, m, CHarom).

The synthetic route of 210532-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIERRE FABRE MEDICAMENT; KALOUN, El Bachir; BEDJEGUELAL, Karim; RABOT, Remi; KRUCZYNSKI, Anna; SCHMITT, Philippe; PEREZ, Michel; RAHIER, Nicolas; US2013/85144; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 50594-82-6, These common heterocyclic compound, 50594-82-6, name is 3,4,5-Trichlorobenzotrifluoride, 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.

STR73 12.5 g (0.05 mol) of 3,4,5-trichloro-benzotrifluoride are added slowly and with stirring to a mixture of 8.0 g (0.05 mol) of 2,7-dihydroxynaphthalene, 4.2 g (0.075 mol) of pulverulent potassium hydroxide and 100 ml of dimethyl sulphoxide, which has been warmed to 60 C., and the reaction mixture is then stirred for a further approx. 3 hours at 60 C. After the mixture has been cooled to approximately 20 C., it is diluted with water and methylene chloride, and filtered. The organic phase is separated off from the filtrate, washed with water, dried using sodium sulphate and filtered. The solvent is removed from the filtrate by distillation in a water-pump vacuum, the residue is stirred with petroleum ether and the product which is thus obtained in the form of crystals is isolated by filtering with suction. 4.9 g (26% of theory) of 7-(2,6-dichloro-4-trifluoromethylphenoxy)-2-naphthol of melting point 98 C. are obtained. In analogy to Example (II-1) the starting substances of the formula (II) listed below in Table 2 may be prepared. STR74

The synthetic route of 50594-82-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US5041609; (1991); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 97329-43-6, A common heterocyclic compound, 97329-43-6, name is 1-Bromo-2-chloro-3-methylbenzene, molecular formula is C7H6BrCl, 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.

Preparation of l-(2-chloro-3-methylphenyl)propan-2-one: A Smith process vial was charged with l-bromo-2-chloro-3 -methylbenzene (528 mg, 2.57 mmol, 1 eq.), tributylmethoxytin (1.11 mL, 1.5 eq.), 4-methylpent-4-en-2-one (0.42 mL, 1.5 eq.), PdCl2 (23 mg, 5%) and tri(o-tolyl)phosphine (79 mg, 10%), toluene (1 mL) was added and mixture sparged with nitrogen for 10 minutes and then heated in oil bath at 100 C for 5 hours. The reaction mixture was diluted with ethyl acetate and washed with brine, dried (MgS04), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes) to l -(2-chloro-3-methylphenyl)propan-2- one (375 mg, 80% yield). 1H-NMR: 400 MHz, (CDC13) delta : 7.19-7.02 (m, 3H), 3.82(s, 2H), 2.38(s, 3H), 2.18 (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; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BJORNSON, Kyla; GUO, Hongyan; HALCOMB, Randall, L.; LINK, John, O.; MCFADDEN, Ryan; MITCHELL, Michael, L.; ROETHLE, Paul; TRENKLE, James, D.; VIVIAN, Randall, W.; XU, Lianhong; WO2012/3497; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. SDS of cas: 63624-28-2

General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.

The synthetic route of 2,4-Dimethoxybenzene-1-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang; Aili; Zhang; Xu; Pharmazie; vol. 74; 2; (2019); p. 73 – 78;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics