Month: August 2021

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. 827-08-7, name is 1,2-Dibromo-3,4,5,6-tetrafluorobenzene, A new synthetic method of this compound is introduced below., Formula: C6Br2F4

4-Bromo-5-methyl-2-phenylthiazole6 (1.2 g, 4.7 mmol) was dissolved in anhydrous THF (20 mL) under argon atmosphere. 1.6 M n-BuLi hexane solution (3.0 mL, 4.8 mmol) was slowly added dropwise to the solution at -78 C, and the mixture was stirred for 1.5 h. Tri-n-butyl borate (1.3 mL, 4.8 mmol) was slowly added to the solution at the temperature, and the mixture was stirred for 2.5 h. An adequate amount of distilled water was added to the mixture to quench the reaction. 1,2-Dibromotetrafluorobenzene (640 mg, 2.1 mmol), tetrakis(triphenylphosphine)palladium(0) (160 mg, 0.14 mmol), and 20 wt% Na2CO3 aqueous solution (7.5 mL) were added to THF (30 mL), and the mixture was refluxed for 6 h. The reaction mixture was neutralized by HCl aqueous solution, extracted with ether, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using n-hexane as the eluent to give 160 mg of 2a in 15% yield based on 1,2-dibromotetrafluorobenzene. The 1H and 13C NMR spectra of 2a are shown in Figure S1. 2a: 1H NMR (300 MHz, CDCl3, TMS) delta = 2.29 (s, 6H, CH3), 7.27-7.37 (m, 6H, Aromatic H), 7.67-7.73 (m, 4H, Aromatic H). 13C NMR (75 MHz, CDCl3) delta = 12.1, 126.3, 128.9, 129.9, 133.4, 133.5, 142.7, 164.5. HR-MS (MALDI) m/z = 497.0762 (MH+). Calcd for C26H17F4N2S2+ = 497.0764.

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; Hamatani, Shota; Kitagawa, Daichi; Kobatake, Seiya; Nakahama, Tatsumoto; Tetrahedron Letters; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 328-70-1, 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 328-70-1 as follows.

A mixed solution of 3,5-bis(trifluoromethyl)phenyl bromide (22.0 g), (R)-3-hydroxypyrrolidine hydrochloride (9.23 g), palladium(II) acetate (0.84 g), (+/-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (4.68 g) and cesium carbonate (73.4 g) in toluene (300 mL)-1,4-dioxane (100 mL) was stirred under an argon gas atmosphere at 80 C. for 16 hr. The solid was filtered off, and the filtrate was washed with saturated brine and water, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate 10:1-3:1) to give the title compound (13.7 g, yield 61%) as a white solid.1H-NMR (300 MHz, CDCl3) delta: 1.74 (br, 1H), 2.06-2.31 (m, 2H), 3.28-3.38 (m, 1H), 3.39-3.50 (m, 1H), 3.50-3.66 (m, 2H), 4.61-4.73 (m, 1H), 6.87 (s, 2H), 7.12 (s, 1H).

According to the analysis of related databases, 328-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kasai, Shizuo; Kamaura, Masahiro; Cho, Nobuo; US2011/251187; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 452-63-1, name is 1-Bromo-4-fluoro-2-methylbenzene, 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 452-63-1, HPLC of Formula: C7H6BrF

1. Preparation of 2-[6-(3-Amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl]-4-fluoro-benzonitrile and Pharmaceutically Acceptable Salts A mixture of 2-bromo-5fluorotoluene (2) (3.5 g, 18.5 mmol) and CuCN (2 g, 22 mmol) in DMF (100 mL) was refluxed for 24 hours. The reaction was diluted with water and extracted with hexane. The organics were dried over MgSO4 and the solvent removed to give product 3 (yield 60%). 1H-NMR (400 MHz, CDCl3): delta 7.60 (dd, J=5.6, 8.8 Hz, 1H), 6.93-7.06 (m, 2H), 2.55 (s, 3H).

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-4-fluoro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Christopher, Ronald J.; Covington, Paul; US2007/60530; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 626-88-0, These common heterocyclic compound, 626-88-0, name is 1-Bromo-4-methylpentane, 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.

37.1 2-[(tert-butoxycarbonyl)amino]-6-methylheptanoic acid A solution of diisopropylamine (13.2 ml; 0.094 mol) in 130 ml of tetrahydrofuran (THF) is cooled down to -40 C. n-butyllithium (37 ml of a 2.5 M solution in hexane; 0.094 mol) is added dropwise. The temperature is allowed to rise to 0 C. At this temperature, Boc-glycine (5 g; 0.028 mol) in solution in 30 ml of THF is introduced into the mixture. The reaction medium is left for ten minutes at this temperature then 1-bromo-4-methylpentane (7.9 ml; 0.056 mol) in solution in 20 ml of THF is added rapidly. The temperature is allowed to return to 23 C. and the mixture is stirred at this temperature for one hour. After hydrolysis with 100 ml of water then acidification with 150 ml of a saturated solution of potassium hydrogen sulphate, the mixture obtained is extracted twice with 50 ml of ethyl acetate. The organic phase is washed with 100 ml of water then with 100 ml of a saturated solution of sodium chloride. After drying over magnesium sulphate and evaporating the solvent, the residue obtained is purified on a silica column (eluent: ethyl acetate-heptane/6-4) in order to produce a white-coloured powder with a yield of 50%.

The synthetic route of 626-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chabrier De Lassauniere, Pierre-Etienne; Harnett, Jermiah; Bigg, Dennis; Liberatore, Ann-Marie; Pommier, Jacques; Lannoy, Jacques; Thurieau, Christophe; Dong, Zheng Xin; US2005/38087; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 7314-86-5, 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. 7314-86-5 name is 1,3,5,7-Tetrabromoadamantane, 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.

A 250 ml three-necked flask equipped with a condenser was charged with 5.0 g (ie, 11. Ommol) of tetrabromoadamantane and 20 mL (ie, leOmmol) of o-methoxybromobenzene. An inverted funnel was pipetted from the upper end of the condenser to a 30% NaOH aqueous solution to absorb the HBr produced by the reaction. Under 5 C cold water bath, 1.2g (S Jie 4.5mmol) of AlBr3 was added to the reaction system, and the reaction was continued under a cold water bath for 1 hour, then the cold water bath was withdrawn and the reaction was resumed to room temperature for about 3 hours. Finally, the reaction system In the oil bath was heated to 60 C for 4 hours, the reaction was cooled to room temperature, poured into 100mL of acidic ice water and stirred lh.After the ice has completely melted, 100 ml of ethyl acetate is added to the mixture for extraction. The organic layer is washed with water until neutral, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and the filtrate is concentrated. The concentrated solution is then slowly added dropwise to 100 ml Methanol, precipitation, to give a pale yellow solid 6.9g, 72% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3,5,7-Tetrabromoadamantane, and friends who are interested can also refer to it.

Reference:
Patent; Chinese Academy Of Sciences Physics And Chemistry Technology Institute; Chen Jinping; Li Yi; Yu Tianjun; Zeng Yi; (20 pag.)CN107324978; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 2550-36-9, 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. 2550-36-9 name is (Bromomethyl)cyclohexane, 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.

[Synthesis of Compound 1]In a three-necked flask, 20 g of bromomethylcyclohexane and 12.5 g of 1-naphthol were dissolved in 300 g of NMP. Thereafter, 12 g of potassium carbonate and 14 g of potassium iodide were added to the solution, and heated at 120 C. for 8 hours. Water amounting to 300 g was added to the thus obtained reaction liquid, and was extracted with 100 g of hexane three times. The obtained organic phases were collected, and washed with 100 g of 1N aqueous sodium hydroxide solution once, with 100 g of water once and with 100 g of brine once. The thus washed organic phase was concentrated, thereby obtaining 13 g of compound 1.An NMR chart of the compound 1 is given in FIG. 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (Bromomethyl)cyclohexane, and friends who are interested can also refer to it.

Reference:
Patent; FUJIFILM CORPORATION; US2012/237874; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 59734-92-8, name is 1-Bromo-2-cyclohexylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 59734-92-8

Example 82; Synthesis of 2-(2-cyclohexylphenylami?o)-3H-benzimidazole-5-carboxylic acid (lH-indazol-6-yl)-amideTo a solution of l-bromo-2-cyclohexyl-benzene (5 mmol) in dioxane (20 mL) was added solid Pd(OAc)2 (0.1 g) and solid CsCO3 (10 mmol). tert-Buty] carbamate (7 mmol) was added to the reaction mixture, and the contents were heated at 80 0C for 2 h. The reaction mixture was cooled to room temperature and filtered through Celite. The solvent was removed in vacuo and the residue obtained was purified by flash column chromatography using DCM as elupsilonant to yield (2-cyclohexylphenyI)-carbamic acid tert-hvtiy ester.The carbamate obtained as above was treated with 4 M HCl in dioxane following the procedure described in Example 80 to afford 2-cyclohexylphenylamine as a hydrochloride salt.To a solution of aforementioned amine hydrochloride (1 mmol) in dry DMF (2 mL) was added DIEA (1.5 mmol) and lj’-thiocarbonylimidazole (1 mmol). The reaction mixture was heated at 700C for Ih to provide l-cyclohexyl-2-isothiocyanatobenzene as described in general procedure A.The isothiocyanate (0.5 mmol) was reacted with 3,4-diamino-N-(lH-mdazol-6-yl)- benzamide (0.5 mmol; see Example 25) according to general procedure B to yield 2-(2- cyclohexylphenylamino)-3H-benzimidazole-5-carboxylic acid (lH-indazol-6-yl)-amide. MS: m/z 451 (M+H)+.

The synthetic route of 59734-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TRANSTECH PHARMA, INC.; WO2007/95124; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 6698-13-1, 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 6698-13-1 as follows.

3-Benzo[1,3]dioxol-4-yl-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-pyridin-3-yl-amineTo a stirred solution of 4-bromo-1,3-benzodioxole (65 mg, 0.323 mmol, 1 eq.) and chloro(di-2-norbornylphosphino)(2’dimethylamino-1,1′-biphenyl-2-yl)palladium (II) (18 mg) in anhydrous dioxane (3 mL) under nitrogen2 is added a dioxane (31 mL) solution of [3-(tert-butyl-diphenyl-silanyloxy)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyridin-3-yl-amine (196 mg, 0.356 mmol, 1.1 eq) followed by 2M aqueous K3PO4 (0.35 mL, 0.7 mmol). The mixture is heated to 100 C. in a sealed tube overnight.The reaction mixture was returned to ambient temperature, and diluted with methylene chloride. The organic phase washed with brine, dried over MgSO4, filtered and concentrated to a dark brown oil. Flash chromatography (1% MeOH/methylene chloride) gave 117 mg of 3-benzo[1,3]dioxol-4-yl-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-pyridin-3-yl-amine as a beige solid.

According to the analysis of related databases, 6698-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Locus Pharmaceuticals, Inc.; US2008/280891; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 348-57-2, A common heterocyclic compound, 348-57-2, name is 1-Bromo-2,4-difluorobenzene, molecular formula is C6H3BrF2, 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 19 Preparation of 4-(2,4-difluorophenyl)-anisole from 4-methoxyphenylmagnesiumbromide and palladium chloride/triphenylphosphine (0.05percent) A suspension of magnesium turnings (1.54 g; 63.3 mmoles – Pometon) in tetrahydrofuran (16.02 g) was heated at 65°C under stirring and under nitrogen. Then, iodine (0.02 g) and, after 30 minutes, 4-bromoanisole (11.69 g; 62.5 mmoles), in 1 hour, were added to the reaction mixture. At the end of the addition, the reaction mixture was kept at 75°C for 1 hour and, then, decanted obtaining a solution of 4-methoxyphenylmagnesiumbromide (solution A). A mixture of 1-bromo-2,4-difluorobenzene (11.4 g; 59.1 mmoles), palladium chloride (0.00526 g; 0.0297 mmoles – Fluka) and triphenylphosphine (0.03088 g; 0.1177 mmoles – Fluka) was de-aerated by vacuum/nitrogen at 25°C. The mixture was heated at 85°C, kept under stirring for 15 minutes and, then, solution A was added in 3 hours. At the end of the addition, the reaction mixture was kept at 85°C for 30 minutes. After cooling at 60°C, a solution of 37percent hydrochloric acid (2 ml) in water (10 ml) was added in 20 minutes. The mixture was cooled at 40°C and the phases were separated. The solvent of the organic phase was evaporated under reduced pressure obtaining the desired compound (98.5percent yield).

The synthetic route of 348-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZAMBON GROUP S.p.A.; EP494419; (1992); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 103-64-0, name is (2-Bromovinyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of (2-Bromovinyl)benzene

General procedure: To a solution of CoBr2 (22 mg, 0.10 mmol, 10 mol%), bis-1,2-diphenylphosphinopropane (41.2 mg, 0.10 mmol, 10 mol%), and manganese powder (165 mg, 3 mmol, 3 equiv) in acetonitrile (5 mL) was added the aryl bromide (2 mmol, 2 equiv) at the desired temperature (rt for the bromo eneformamides or 40C for the bromo enecarbamates). A solution of the bromo eneformamide (1 mmol, 1 equiv) in acetonitrile (5 mL) was added slowly. After completion (as judged by TLC and GC-MS), the reaction mixture was treated with a mild acid such as 10% H3PO4 (aq) and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to afford the desired coupling product as an oil. Purification was carried out by flash chromatography on silica (pretreated with 1% Et3N).

The synthetic route of 103-64-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bassler, Daniel P.; Alwali, Amir; Spence, Laura; Beale, Oliver; Beng, Timothy K.; Journal of Organometallic Chemistry; vol. 780; (2015); p. 6 – 12;,
Bromide – Wikipedia,
bromide – Wiktionary