Tag: M.W=100-200

Synthetic Route of 39478-78-9,Some common heterocyclic compound, 39478-78-9, name is 5-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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.

Tetrakis(triphenylphosphine)palladium (0) (3.7 g, 0.003 mol) and 4-chlorophenylboronic acid (20.2 g, 0.13mol) are added to a solution of 5-bromo-2-methylaniline (20 g, 0.1 mol) in 1 ,2- dimethoxyethane (200 ml). After stirring the reaction mixture for 15 minutes at 200C, a solution of 20% aqueous sodium carbonate (300ml) is added to the mixture, and the resulting mixture is heated at reflux for 24 hours. The reaction mixture is cooled to room temperature, diluted with water (600 ml) and extracted using ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with 7% ethyl acetate in hexane to give 3-amino-4′-chloro-4-methylbiphenyl (21.0 g).

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

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; WO2009/150093; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 21120-91-2, 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. 21120-91-2, name is 7-Bromobicyclo[4.2.0]octa-1,3,5-triene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Magnesium turnings (210 mg), sodium hydride (29 mg, 60% oil dispersion) and a magnetic stir bar were added to a 100 ml rbf, capped with a rubber septum and placed under vacuum and allowed to stir for 4 hours. A solution of BrBCB (750 mg) in THF (20 ml) was added via syringe slowly. The solution turned bright yellow and was placed under a nitrogen atmosphere. The solution was left to stir for 30 minutes then added via syringe to a 100 ml rbf containing a stir bar, bromostyrene (1 g), Pd PEPPSI-iPr (1,3-Bis(2,6-Diisopropylphenyl)imidazol-2-ylidene)(3-chloropyridyl)palladium(II) dichloride, CAS no: 905459-27-0) catalyst (190 mg, 5 mol %) and THF (15 ml ) under nitrogen and capped with a rubber septum. The mixture turned black after about 30 minutes and was left to stir at room temperature for 12 h. The mixture was added to a separatory funnel containing water (100 ml), and extracted with ethyl acetate (3¡Á100 ml). The combined organics were dried with brine (100 ml) and sodium sulfate, filtered and concentrated in vacuo. The residue was recrystallized in methanol to give the desired product as a colorless solid (203 mg, 18% yield). 1H NMR (500 MHz, Chloroform-d) delta 7.49 (d, J=8.1 Hz, 2H), 7.44-7.26 (m, 6H), 6.84 (dd, J=17.7, 10.8 Hz, 1H), 5.86 (d, J=17.7 Hz, 1H), 5.35 (d, J=10.8 Hz, 1H), 4.86-4.75 (m, 1H), 3.85 (dd, J=13.9, 5.7 Hz, 1H), 3.22 (dd, J=13.9, 2.7 Hz, 1H). A DSC of the resulting monomer showed an exotherm (cure) peak max of 165 C. at a scan rate of 10 C./min. (0070) The yield in the above reaction was very low. Further, no ether linkage resulted from the reaction. However, the cure temperature of the monomer was acceptable.

The synthetic route of 7-Bromobicyclo[4.2.0]octa-1,3,5-triene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Electronic Materials LLC; Hayes, Colin; Gallagher, Michael K.; Riener, Michelle; (10 pag.)US2019/169327; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 103-64-0, A common heterocyclic compound, 103-64-0, name is (2-Bromovinyl)benzene, molecular formula is C8H7Br, 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.

At room temperature,To the appropriate amount of the organic solvent DMF was added 100 mmol of the compound of the above formula (I)250 mmol of the compound of formula (II)4 mmol of catalyst (1 mmol of Pd (TFA) 2 with 3 mmol of Cu (acac) 2)35 mmol of 1-ethyl ethyl ether-3-methylimidazolebis (trifluoromethanesulfonyl) imide salt and 250 mmol of triisopropanolamine,Then heated to 70 C,And the reaction was stirred at that temperature for 8 hours; After the reaction,The resulting mixture was filtered while hot,To obtain a filtrate;To the filtrate was added a 10% hydrochloric acid solution with a mass percentage of 10%Adjust the pH to neutral;Then ethyl acetate,Oscillation extraction 2-3 times,Combined organic phase,Dried over anhydrous magnesium sulfate,Then concentrated under reduced pressure,The resulting residue was subjected to 200-300 mesh silica gel column chromatography,The petroleum ether-n-butanol mixture was used as the eluent,Wherein the volume ratio of petroleum ether to n-butanol is 9: 1,Thereby obtaining a compound of the above formula (III)The yield was 97.3%.

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; Qingdao University; Xia Yunqiu; Zhou Yingbin; Wang Yanxin; Zhong Weizhen; Guo Shenbo; (9 pag.)CN104803912; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1422-53-3,Some common heterocyclic compound, 1422-53-3, name is 2-Bromo-4-fluorotoluene, molecular formula is C7H6BrF, 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.

The compound of formula 3 (5.0 g, 26.5 mmol, 1.0 equiv) and 98% concentrated sulfuric acid (50 ml) were added to a 100 ml three-necked flask.The solution was cooled to 0 C to 5 C and potassium nitrate (3.5 g, 34.6 mmol, 1.3 equiv) was added in portions.And reacted at 25 C for 2 hours under nitrogen protection. After completion of the reaction, the reaction solution was poured into a large amount of ice water,Ethyl acetate extraction. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, Concentrate under reduced pressure. The crude product was purified by silica gel column chromatography (petroleum ether) to give 3.4 g of the compound of formula 4 as a yield of 54.3%.

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

Reference:
Patent; Shanghai Acebright Pharmaceuticals Group Co., Ltd.; Yu, Libing; Guo, Maojun; Yang, QinGang; Liu, Huixin; (23 pag.)CN105646333; (2016); A;,
Bromide – Wikipedia,
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Some common heterocyclic compound, 1422-54-4, name is 2-Bromo-6-fluorotoluene, molecular formula is C7H6BrF, 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. Formula: C7H6BrF

0.867 g (35.67 mmol) of magnesium turnings were dried and suspended in 17 ml of anhydrous THF under argon. A solution of 1 ,2-dibromoethane (0.14 ml, 1.62 mmol) and 2-bromo-6-fluoro-toluene (6.74 g, 35.67 mmol) in 17 ml of anhydrous THF was then added dropwise so as to maintain a gentle reflux. Once the magnesium had been consumed, copper(l) iodide (0.432 g, 2.27 mmol) was then added, followed by a solution of epichlorohydhne (3.00 g, 32.42 mmol) in DMF (8 ml). The mixture was stirred for 3.5 h at room temperature and then quenched with a saturated solution of ammonium chloride (120 ml). The organic layer was separated, and the aqueous phase was extracted twice with EA. The combined organic phases were washed twice with a saturated solution of ammonium chloride, dried over sodium sulfate, filtered and evaporated to dryness. The product was purified by chromatography on silica gel (cyclohexane/EA, from 100:0 to 90:10) to give 6.89 g of 1-chloro-3-(3-fluoro- 2-methyl-phenyl)-propan-2-ol. 3.92 g (16.23 mmol) of this alcohol were dissolved in DCM under argon, and 1 ,1 ,1-thacetoxy-1 ,1 -dihydro-1 ,2-benziodoxol-3(1 H)-one (Dess-Martin periodinane reagent; 7.57 g, 16.23 mmol) was added. The mixture was stirred at room temperature overnight and then diethyl ether (150 ml) was added. The mixture was washed three times with 1 N hydrochloric acid (70 ml) and twice with a saturated solution of sodium chloride, and extracted with ether. The extracts were dried over sodium sulfate, filtered and evaporated to dryness. 2.69 g of the title compound were obtained as a white powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1422-54-4, its application will become more common.

Reference:
Patent; SANOFI-AVENTIS; STEINHAGEN, Henning; SCHEIPER, Bodo; MATTER, Hans; MCCORT, Gary; BEGIS, Guillaume; GOBERVILLE, Pascale; THIERS, Berangere; WO2011/12538; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 2550-36-9, name is (Bromomethyl)cyclohexane, A new synthetic method of this compound is introduced below., Recommanded Product: (Bromomethyl)cyclohexane

After 500 mg of hydroxyphthalimide (Aldrich) was dissolved in 5 ml of dimethylformamide under argon flow, 0.47 ml of (bromomethyl)cyclohexane (Aldrich) was added, and 0.5 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (Aldrich) was slowly added. After the mixture was stirred at 60 C. for 2 hours, the temperature was again lowered to room temperature, and then the reaction was stopped by adding a 2 N hydrochloric acid solution. The reaction liquid was diluted by adding 20 ml of ethyl acetate, followed by drying over magnesium sulfate and then filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) and then dried to obtain 787 mg of a compound (yield: 99%). 400 mg of the obtained compound was dissolved in 5 ml of dichloromethane, and 0.14 ml of methyl hydrazine (TCI) was slowly added at 0 C. After the reaction liquid was stirred at room temperature for 2 hours, the temperature was again lowered to 0 C. The generated solid was then filtered out, and 1 ml of a 4 M-hydrochloric acid dioxane solution (Aldrich) was added to the residual filtrate, followed by filtration and drying, to obtain 240 mg of a solid (yield: 94%). 21 mg of the obtained solid and 50 mg of SAC-0906 obtained as obtained above were dissolved in 1 ml of pyridine (Aldrich) under argon flow, followed by stirring at 80 C. for 4 hours. After the temperature was lowered to room temperature, the reaction liquid was acidified by adding a 2 N hydrochloric acid solution, followed by extraction with 20 ml of diethyl ether, drying over magnesium sulfate, and filtering. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) to obtain the target compound SAC-1103 (50 mg, yield: 82%). 1H-NMR (400 MHz, CDCl3) delta 5.87-5.78 (m, 2H), 5.35-5.34 (m, 1H), 5.29-5.26 (m, 1H), 5.16 (m, 1H), 4.24-4.14 (m, 3H), 3.86-3.76 (m, 2H), 3.58-3.51 (m, 1H), 2.41-0.61 (m, 46H)

The synthetic route of 2550-36-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kwon, Young-Gune; Suh, Young-Ger; US2014/378399; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 7745-91-7, name is 3-Bromo-4-methylaniline, A new synthetic method of this compound is introduced below., COA of Formula: C7H8BrN

A cooled (0 0C) solution of 3-bromo-4-methylaniline (ABCR; 1.00 g; 5.37 mmol) in pyridine (20 ml) was treated with methanesulfonyl chloride (500 mul; 6.45 mmol). The reaction mixture was allowed to warm to RT and stirred for 1 hour, then EtOAc was added and the organic layer was washed with a 1 N aqueous solution of HCI. The organic layer was dried over MgSO4, filtered and concentrated to dryness to give the title compound as a brown solid (1.42 g, quantitative).1H NMR (300MHz, DMSO-d6) delta [ppm] 9.81 (1 H, s), 7.40 (1 H, d, J= 2.1 Hz), 7.31 (1 H, d, J= 8.3 Hz), 7.13 (1 H, d, J= 8.3 Hz, J= 2.1 Hz), 2.99 (3H, s), 2.29 (3H, s)

The synthetic route of 7745-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; CROSIGNANI, Stefano; JORAND-LEBRUN, Catherine; CLEVA, Christophe; PRETRE, Adeline; WO2010/92043; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 10485-09-3, 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 10485-09-3 as follows.

(3) Synthesis of 2-(1H-indene-2-yl)naphthalene Finally, 2.7 g (13.8 mmol) of 2-bromoindene was added to a 100 mL Schlenk flask, and dissolved in a mixed solution of 60 mL of DME (dimethyl ether) and 20 mL of water. 3.4 g (18 mmol) of 2-naphthalene boronic acid and 2.8 g (21 mmol) of K2CO3 were added thereto, and argon gas was bubbled therein for 10 min to remove oxygen in the solvent. Thereafter, heating was initiated under an argon atmosphere, and when the temperature reached 90 C., 800 mg (0.7 mmol, 5 mol %) of palladium(0)tetrakis(triphenylphosphine) (Pd/C) was added thereto, and stirred for 6 h. Thereafter, the reaction mixture was cooled to room temperature, and 200 mL of water was poured thereto to filter the resulting brown precipitate, which was washed with about 50 mL of ether, and then dried, thereby obtaining 2.4 g (67%) of a white solid. 1H NMR (500 MHz, CDCl3): delta 3.96 (2H, s), 7.23 (1H, m), 7.31 (1H, m), 7.48-7.54 (4H, m), 7.69-7.74 (1H, m), 7.76-7.83 (4H, m), 8.01 (1H, s).

According to the analysis of related databases, 10485-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG CHEM, LTD.; KIM, Se Young; CHO, Min Seok; KIM, Dae Hwan; LEE, Sung Min; PARK, Sung Ho; LEE, Ki Soo; HONG, Bog Ki; LEE, Yong Ho; CHO, Kyung Jin; HAN, Chang Woan; PARK, Jin Young; (13 pag.)US2016/194422; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 55289-36-6, name is 3-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8BrN

[0249] (a) 4-Bromoindazole. A 350 mL 5-necked flask was charged with benzene (127 mL) and potassium acetate (4.24 g, 43.2 mmol). 3-Bromo-2- methyl-aniline (6.00 g, 42.4 mmol) was added over a period of 5 min to the white suspension followed by acetic anhydride (12.0 mL, 127 mmol). A thick white suspension was formed at this point. The mixture was heated to 80C and isopentyl nitrite (8.46 g, 43.2 mmol) was added and the orange suspension was heated at 80C overnight. The reaction mixture was cooled, filtered and the filter cake was washed with benzene (3×30 mL). The filtrate was concentrated under reduced pressure to remove the solvent and the residue was heated to 60C. Cone. HCl (2.0 mL) was added and the mixture was stirred at 7O0C for 1 h. More cone. HCl was added (2.0 mL) and the mixture was stirred at 70C for 3 h. The mixture was cooled, diluted with water and toluene until the solid was completely dissolved. The layers were separated and the aqueous layer was extracted with toluene (3×50 mL). The combined organics were concentrated until product began to crystallize. The suspension was cooled to 0C and the precipitated solid was filtered to provide 4-bromoindazole as a beige solid (4.45 g, 53%).

The synthetic route of 55289-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; WO2008/8059; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 630-17-1, name is 1-Bromo-2,2-dimethylpropane, belongs to bromides-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 630-17-1, COA of Formula: C5H11Br

Example 2: Synthesis of posphoric acid mono-[2-(2, 2-dimethyl-propane-1-sulfonyl)-ethyl] ester A. 2-(2, 2-Dimethyl-propane-1-sulfonyl)-ethanol; A suspension of 2-mercapto-ethanol (110 mg, 1.41 mmol), 1-bromo-2, 2-dimethyl-propane (210 mg, 1.41 mmol) and K2C03 (195 mg, 1.41 mmol) in DMF (3 mL) was stirred at 60 C for 5 h. The reaction mixture was then cooled to room temperature and treated with a mixture of 2KHS05-KHS04 (1.30 g, 2.11 mmol) in water (0.5 mL). After stirring for 12 h at room temperature, the solvent was removed in vacuo, and the residue partitioned between ethyl acetate and water. The organic layer was dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by flash chromatography over silica gel (elution with hexane/ethyl acetate 4: 1) to give the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) 6 1.23 (s, 9H), 2.55 (s br. , 1H), 3.05 (s, 2H), 3.18-3. 23 (m, 2H), 4.09-4. 19 (m, 2H).

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; JERINI AG; WO2005/80406; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary