Tag: M.W=200-300

Synthetic Route of 203302-92-5, A common heterocyclic compound, 203302-92-5, name is 3-Bromo-2-chloro-6-fluorotoluene, molecular formula is C7H5BrClF, 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.

11. Reactions which are covered by Scheme 11; Example 11.1 : Preparation of (3-bromo-2-chloro-6-fluoro-phenyl)-acetic acid; Step 1; 3-Bromo-2-chloro-6-fluoro-toluene (8.0 g), N-bromosuccinimide (NBS) (6.42 g) and a catalytic amount of benzoyl peroxide in carbon tetrachloride (40 ml) were heated to reflux. A 500 watt tungsten halogen lamp was used to initiate the reaction. The reaction mixture was heated to reflux and irradiated for 30 minutes. The reaction mixture was allowed to cool and then filtered. The filtrate was concentrated to give a colourless oil which solidified on standing to give l-bromo-3-bromornethyl-2-chloro-4-fluorobenzene as an off-white solid (10.7 g). 1H NMR (CDCl3): 4.64 (d, 2H), 6.94 (t, IH), 7.58 (dd, IH) ppm.

The synthetic route of 203302-92-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA LIMITED; WO2008/9908; (2008); A1;,
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Some common heterocyclic compound, 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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. Application In Synthesis of 2,4-Difluorobenzene-1-sulfonyl chloride

General procedure: To 5-(5-(5-Aminopyridin-3-yl)thiophen-2-yl)-2-methyl- isoindolin-1-one (49) (225 mg, 0.79 mmol) in dry pyridine (23 mL) under N2 at RT,was added dropwise, 2,4-difluorobenzenesulphonyl chloride (336 mg, 1.58 mmol) in CH2Cl2(3 mL) over 5 min. The suspension was heated to 45 C under N2 for 4 h., at which pointanother portion of 2,4-difluorobenzenesulphonyl chloride (169 mg, 0.79 mmol) in CH2Cl2 (2mL) was added. The whole mixture was left to stir for at 45 C under N2 for 16 h., then thesolvent removed under reduced pressure. The resulting residue was suspended in acetone (10mL), 1 M HCl (20 mL) added, and the entire mixture stirred for 10 minutes. The solid wasthen collected by filtration, washed well with 1 M HCl and water, dried, and purified bychromatography as described below. In cases where the bis-sulphonamide was also formed, a second step was introduced wherethe crude product above was treated with a 1:1 mixture of 1,4-dioxane and 2 M NaOH. Thecrude sulphonamide resulting from subsequent acidification of the reaction mixture wasisolated by filtration, washed well with water, and dried. Purification was carried out by flashcolumn chromatography (2% MeOH/CH2Cl2 as eluant), giving the title compound as a paleyellow solid (211 mg, 545).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13918-92-8, its application will become more common.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
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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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, A new synthetic method of this compound is introduced below., COA of Formula: C13H11ClFNO

A stirred suspension of 3H-6-iodoquinazolin-4-one (compound A) in toluene (5 vols) was treated with tri-n-butylamine (1.2 eq.) at 20 to 250C, then heated to 900C. Phosphorous oxychloride (1.1eq) was added, the reaction mixture was then heated to reflux. The reaction mixture was cooled to 500C and toluene (5vols) added. Compound C (1.03 eq.) was added as a solid, the slurry was warmed back to 900C and stirred for 1 hour. The slurry was transferred to a second vessel; the first vessel was rinsed with toluene (2vol) and combined with the reaction mixture. The reaction mixture was cooled to 700C and 1.0 M aqueous sodium hydroxide solution (16 vols) added dropwise over 1 hour to the stirred slurry maintaining the contents temperature between 68-72C. The mixture was stirred at 65-700C for 1 hour and then cooled to 200C over 1 hour. The suspension was stirred at 200C for 2 hours, the product collected by filtration, and washed successively with water (3 x 5 vols) and ethanol (IMS, 2 x 5 vols), then dried in vacuo at 50-600C. Volumes are quoted with respect of the quantity of Compound A used. Percent yield range observed: 90 to 95% as white or yellow crystals.

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; SMITHKLINE BEECHAM (CORK) LIMITED; WO2006/66267; (2006); A2;,
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Reference of 14862-52-3, A common heterocyclic compound, 14862-52-3, name is 3,5-Dibromochlorobenzene, molecular formula is C6H3Br2Cl, 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.

3 -Bromo-5 -chlorophenvDmethylformamide l,3-Dibromo-5-chlorobenzene (1.0 g, 3.7 mmol), N-methylformamide (0.26 mL, 4.4 mmol), CuI (35 mg, 0.02 mmol), N,N’-dimethyl ethylenediamine (0.04 mL, 0.37 mmol) and K2CO3 (1.02 g, 7.4 mmol) in 1,4-dioxane (4 mL) were heated to 110 0C in a sealed tube for 20 h. The blue slurry was diluted with EtOAc (10 mL) and filtered through a short silica plug that was washed with several portions of EtOAc. The solvent was removed by evaporation and the resulting yellow oil was purified by flash chromatography using 70 g silica and a gradient of 0%EtOAc to 50%EtO Ac/Heptane. The subtitle compound was obtained as a colourless solid (385 mg, 41%).1H-NMR (CDCl3): delta 8.52 (IH, s), 7.43 (IH, t), 7.24 (IH, t), 7.13 (IH, t), 3.30 (3H, s); GC-MS m/z: 247/249/251 [M+].

The synthetic route of 14862-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/7747; (2009); A2;,
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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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1996-29-8

First Step Under argon atmosphere, a mixture of 9H-carbazole (9.3 g), 1-bromo-4-chloro-2-fluorobenzene (23.3 g), cesium carbonate (36.2 g), and DMF (222 mL) was stirred at 150 C. for 7 h. After adding water at room temperature, the resultant mixture was extracted with ethyl acetate. The organic layer was purified by silica gel column chromatography, and then, the solvent was removed to obtain 9-(2-bromo-5-chlorophenyl)carbazole as a white solid (11.4 g, 58% yield).

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; IDEMITSU KOSAN CO., LTD.; HAKETA, Tasuku; ITO, Hirokatsu; KUDO, Yu; (306 pag.)US2018/182974; (2018); A1;,
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Related Products of 57310-39-1, 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. 57310-39-1 name is 3-Bromo-4-chlorotoluene, 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.

In a reactor equipped with a reflux condenser, a mixture of 3-bromo-4-chlorotoluene (compound CM20a above, 30.82 g, 150 mmol), 2,5-dimethylphenylboronic acid (compound CM20b above, 24.75 g, 165 mmol), anhydrous potassium carbonate (124.39 g, 900 mmol), palladium(II) acetate (0.67 g, 6 mmol), tricyclohexylphosphine (1.68 g, 12 mmol), dimethylacetamide (commercially available dehydrated product, 600 ml) and pivalic acid (15.32 g and 150 mmol) was stirred for 10 hours under an argon gas atmosphere while heating in an oil bath set to 150 C. After diluting with toluene (500 ml), rinsing and liquid separation were carried out 3 times using ion-exchanged water. Next, there was repeated twice a procedure of adding active white clay (product of Wako Pure Chemical Industries, Ltd., 60 g) to the obtained oil layer, stirring the mixture for 2 hours, and then passing it through Celite and a silica gel pad to remove the insolubles. After removing the solvent from the obtained solution by concentration under reduced pressure, recrystallizing purification was carried out (with a mixed solvent of chloroform and ethanol), and the deposited crystals were filtered out and dried under reduced pressure to obtain the target CM20c (35.5 g) as a solid with a faint yellow-white appearance. Yield: 51%. The HPLC-area percent value of the obtained compound CM20c measured under analysis conditions 1 was 99.3% (UV254 nm)

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

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMTIED; Cambridge Display Teclmology Limited; Sekine, Chizu; Mikami, Satoshi; Anryu, Makoto; Kakimoto, Hidenobu; Steudel, Annette Regine; Humphries, Martin John; Kamtekar, Kiran Timothy; Garcia, Elena Hojas; Heidenhain, Sophie; Pegington, Ruth; (144 pag.)US9929347; (2018); B2;,
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Reference of 62356-27-8, A common heterocyclic compound, 62356-27-8, name is 1-Bromo-3-chloro-2-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.

EXAMPLE 175 6-(3-chloro-2-methylphenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 275, structure 4 of Scheme lI, where R1 =3-chloro-2-methylphenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (70.0 mg, 0.22 mmol) and 2-bromo-6-chlorotoluene (45.2 mg, 0.22 mmol). The crude material was purified by flash column chromatography (75 ml silica, hexane to 5% ethyl acetate/hexane) to afford 63.1 mg (96%) of Compound 275. Data for Compound 275: 1 H NMR (400 MHz, acetone-d6) 7.30 (d, J=8.3, 1 H), 7.16 (m, 1 H), 6.95 (s, 1 H), 6.87 (d, J=10.2, 1 H), 6.54 (d, J=8.0, 1 H), 5.36 (s, 1 H), 5.25 (s, 1 H), 2.03 (s, 3 H), 1.28 (s, 6 H).

The synthetic route of 62356-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5696130; (1997); A;,
Chloride – Wikipedia,
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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 14862-52-3 as follows. Quality Control of 3,5-Dibromochlorobenzene

Under an argon atmosphere, 1,3-dibromo-5-chlorobenzene (2.70 g, 10.0 mmol) was dissolved in THF (38 mL). The mixture was cooled to -15 C., a THF solution (0.86 M, 12.3 mL, 10.5 mmol) of isopropyl magnesium chloride / lithium chloride complex was added, and the temperature was raised to 0 C. over 3 hours. Cyanuric chloride (5.53 g, 30.0 mmol) was added to the reaction mixture at the same temperature, then the temperature was raised to room temperature and stirred for 24 hours. Saturated ammonium chloride aqueous solution was added to the reaction mixture to stop the reaction, and then ethyl acetate was added. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, washed with water and dried over sodium sulfate.After filtering off the solid, the low-boiling fraction was removed under reduced pressure and the resulting residue was dried under vacuum to give crude product (6.74 g). The obtained crude product (6.6 g) was heated to 40 C. for 4 hours under reduced pressure (8 Pa), then heated to 50 C. and heated for 12 hours. After cooling to room temperature, purification by silica gel chromatography (eluent: hexane / ethyl acetate) gave the desired 2- (3-bromo-5-chlorophenyl) -4,6- dichloro-1,3,5- Triazine (82%, 2.80 g, 8.2 mmol).

According to the analysis of related databases, 14862-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH INSTITUTE; AIHARA, HIDENORI; SHONO, TOMOHIRO; (35 pag.)JP2017/160145; (2017); A;,
Chloride – Wikipedia,
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Synthetic Route of 98-60-2,Some common heterocyclic compound, 98-60-2, name is 4-Chlorobenzenesulfonyl chloride, molecular formula is C6H4Cl2O2S, 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: The substance was synthesized according to a previously reported procedure with some modifications.[3] To a stirred and warmed (80 oC) solution of Na2SO3 (2.36 g, 19 mmol) and NaHCO3 (1.68 g, 20 mmol) in 100 mL H2O was added portionwise arylsulfonyl chloride (10 mmol). The mixture was stirred at 90 C for 3 h, then filtered, and the filtrate concentrated under vacuum. The residue was recrystallised from water (5 mL) to yield the corresponding sodium arylsulfinate.

The synthetic route of 98-60-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Xinxin; Chen, Fei; Lu, Guo-Ping; Tetrahedron Letters; vol. 59; 48; (2018); p. 4226 – 4230;,
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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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

l-Bromo-4-chloro-2-fluorobenzene (20.51 g, 97.93 mmol) was stirred in THF under nitrogen and the r.m. cooled to -15 C. Isopropylmagnesium chloride (2 M in THF, 59.8 mL, 119.6 mmol) was added dropwise at -15 C. The r.m. was stirred at 0-5 C for 1 h, then cooled to -15 C. Intermediate 4 (10 g, 48.97 mmol) dissolved in THF (total amount of THF 120 mL) was added dropwise and the mixture was allowed to reach r.t. NH4C1 sat. sol. was then added dropwise and the r.m. extracted with DCM. The organic layer was dried over MgS04, filtered and concentrated in vacuo. The product was purified by flash column chromatography (silica, MeOH/DCM 0/100 to 4/96). The purest fractions were evaporated, yielding intermediate 49 (8.3 g, 51%).

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 1996-29-8.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; VOS, Ann, Marleen; OEHLRICH, Daniel; GIJSEN, Henricus, Jacobus, Maria; WATTS, Karl, Shawn; BHAT, Sathesh, Pangala; VAN DEN KEYBUS, Frans, Alfons, Maria; (151 pag.)WO2018/162443; (2018); A1;,
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