Tag: M.W=100-200

Some common heterocyclic compound, 4117-09-3, name is 7-Bromo-1-heptene, molecular formula is C7H13Br, 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 7-Bromo-1-heptene

To a solution of methyl isobutyrate (2g; 19.60 mmol) in 25ml of THF at -78C was added lithium diisopropylamide (2.0M, 1.2 equiv; 11.77ml) dropwise. After 30 minutes, a solution of 7-bromo-1-heptene (1.2 equiv; 4.14g) in 5ml of THF was added slowly. The reaction was stirred at room temperature for 1-2 hours (until TLC showed completion), then it was diluted with ether and washed with 1M HCl, then water and finally brine. It was dried over sodium sulfate and purified on silica gel (5% ethyl acetate/hexane) to yield 3.25g (87%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4117-09-3, its application will become more common.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH & HUMAN SERVICES; KEYES, Gregory; RAMSDEN, Christopher; (158 pag.)WO2019/10414; (2019); A1;,
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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. 4117-09-3, name is 7-Bromo-1-heptene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4117-09-3

To a solution of ethyl 2-oxocyclopentane-l -carboxylate (3.56 mL, 26.7 mmol, 1 equiv.) in acetone (62 mL) at r.t. was rapidly added potassium carbonate (8.43 g, 60.4 mmol, 2.25 equiv.) and potassium iodide (1.43 g, 8.55 mmol, 0.32 equiv.). After stirring for 10 min, a solution of 7-bromohept-l-ene (4.23 mL, 26.9 mmol, 1.01 equiv.) in acetone (17 ml) was added and the reaction was refluxed for 23 h. Diethyl ether (100 mL) was added, the mixture was filtered on a Celite pad and the solvent was evaporated. The residue was diluted with ether, washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford ethyl l-(hept-6-en-l-yl)-2-oxocyclopentane-l -carboxylate as an oil (6.37 g, 88 % purity, 92 % yield).

The synthetic route of 4117-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FIRMENICH SA; COULOMB, Julien; DEMOLE, Edouard; (29 pag.)WO2020/78892; (2020); A1;,
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Some common heterocyclic compound, 626-88-0, name is 1-Bromo-4-methylpentane, molecular formula is C6H13Br, 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 1-Bromo-4-methylpentane

General procedure: The solution of dihydroxyacetophenone (1, 1.0equiv), anhydrous potassium carbonate (2.0equiv) and corresponding alkyl bromides (2, 1.1equiv) in acetonitrile was stirred at 70-80C for 4-5h. After evaporation of acetonitrile, the reaction mixture was diluted with dichloromethane and washed with water three times. The organic layer was dried with anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography to give 3. 6.1.1.2 1-(2-Hydroxy-6-(4-methylpentyloxy)phenyl)ethanone (3b) Yield 45%; light green liquid; Rf 0.60 (1:9 EA: HX); IR (KBr) 3335, 2917, 2850, 1618 cm-1; 1H NMR (CDCl3) delta 13.26 (s, 1H), 7.31 (t, J = 8.2 Hz, 1H), 6.54 (dd, J = 0.8, 8.4 Hz, 1H), 6.36 (d, J = 8.2 Hz, 1H), 4.01 (t, J = 6.5 Hz, 2H), 2.70 (s, 3H), 1.92-1.85 (m, 2H), 1.58-1.51 (m, 1H), 1.38-1.31 (m, 2H) 0.84 (d, J = 6.5 Hz, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 626-88-0, its application will become more common.

Reference:
Article; Venkateswararao, Eeda; Sharma, Vinay K.; Yun, Jieun; Kim, Youngsoo; Jung, Sang-Hun; Bioorganic and Medicinal Chemistry; vol. 22; 13; (2014); p. 3386 – 3392;,
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Adding a certain compound to certain chemical reactions, such as: 1422-54-4, name is 2-Bromo-6-fluorotoluene, 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 1422-54-4, HPLC of Formula: C7H6BrF

Sodium benzyloxide was prepared by adding benzyl alcohol (20 mmol) to a suspension of NaH (20 mmol) in N-methylpyrrolidone . The freshly prepared solution (10.8 mmol) was added to 1- bromo-3-fluoro-2-methylbenzene (5.41 mmol) in N methylpyrrolidone . The reaction was heated at 100 C and was monitored by TLC until complete consumption of the starting material. Water and ethyl acetate were added, the aqueous layer was separated and the organic layer was washed with water, dried over MgS04, filtered and concentrated. The residue was chromatographed with hexane/EtOAc mixture. Yield: 92%. 1H NMR (500 MHz, CDC13) delta 7.49-7.39 (m, 4H) , 7.37 (d, J = 7.0 Hz, 1H) , 7.20 (d, J = 8.0 Hz, 1H) , 7.02 (t, J = 8.1 Hz, 1H) , 6.86 (d, J = 8.2 Hz, 1H) , 5.09 (s, 2H) , 2.41 (d, J = 3.3 Hz, 3H) . 13C NMR (126 MHz, CDC13) delta 157.5, 137.0, 128.6, 128.0, 127.3, 127.3, 127.2, 126.0, 125.0, 110.7, 70.5, 16.0. MS (EI) m/z 277 (M+) .

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; RIJKSUNIVERSITEIT GRONINGEN; DOeMLING, Alexander; (85 pag.)WO2017/118762; (2017); A1;,
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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 1647-26-3 as follows. Recommanded Product: 1647-26-3

EXAMPLE 8 5-[N-(2-cyclohexyl)-ethyl]-amino-2-(3,5-diethoxyphenyl)-2-isopropylvaleronitrile 30.4 g (0.1 mole) of 5-amino-2-(3,5-diethoxyphenyl)-2-isopropylvaleronitrile and 19.1 g (0.1 mole) of 2-bromoethylcyclohexane gave, after chromatographic purification of the product, 25.7 g (62%) of the base, the procedure used being similar to that described in Example 5.

According to the analysis of related databases, 1647-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF Aktiengesellschaft; US4940780; (1990); A;,
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Electric Literature of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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.

A 500 mL three-necked flask was charged with benzophenone (79.8 g, 0.438 mol), trimethyl orthoformate (69.6 g,0.656 mol), p-toluenesulfonic acid (3.4 g, 0.02 mol) and methanol300mL, open the stirring, heat to reflux, heat for 3 hours, cool down and dilute the solvent under reduced pressure, add the product obtained in the previous step (62.4g, 0.438mol) and 300mL of toluene, increase to 80-110 degrees for 3 hours, increase the temperature The solvent was distilled off under normal pressure until the disappearance of the starting material by GC. The temperature was lowered, and the solvent was concentrated under reduced pressure to give a crude product 136.2 g, dissolved in 1.2 L acetonitrile, transferred to a 2 L reaction flask, and tetrabutylammonium bromide (282.1 g, 0.875) was added. Mol), copper bromide (0.98g, 0.004mol), tert-butyl nitrite (54.1g, 0.525mol) was added dropwise at 0-10 C, stirred at room temperature for 6 hours, TLC controlled material was completely reacted, hydrogen peroxide was added dropwise Sodium (73.5 g, 0.875 mol) dissolved in 600 mL of water, followed by 3-bromo-4-fluoroaniline (124.7 g, 0.656 mol), heated to 50 C, stirred for 1 hour, TLC controlled raw material reaction was complete, cooling , joinThe mixture was combined with EtOAc (EtOAc m.The obtained crude product was recrystallized from ethyl acetate / n-hexane to afford 137.4 g.Yield 65.4%

The synthetic route of 656-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Jinlu Pharmaceutical Technology Co., Ltd.; Gao Feng; Zeng Sailan; Jiang Junqiang; Zhang Xingxing; (8 pag.)CN108003112; (2018); A;,
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These common heterocyclic compound, 1422-53-3, name is 2-Bromo-4-fluorotoluene, 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. COA of Formula: C7H6BrF

Reference Example 3 Production of 5-fluoro-2-methylbenzaldehyde: Iodine (about 1 mg) was added to a mixture of magnesium (26.28 g) and tetrahydrofuran (600 ml) and 2-bromo-4-fluorotoluene (200.4 g) was added dropwise thereto with ice-cooling (the inner temperature was kept at 65C or lower). After completion of the dropwise addition, the mixture was stirred for 1 hour to prepare a Grignard reagent.

The synthetic route of 2-Bromo-4-fluorotoluene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1229019; (2002); A1;,
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Adding a certain compound to certain chemical reactions, such as: 556-96-7, name is 1-Bromo-3,5-dimethylbenzene, 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 556-96-7, Formula: C8H9Br

General procedure: To a mixture of copper salt (0.3 mmol) and ligand 3 (0.8mmol) in DMF (2.5 mL), aryl halide (1.0 mmol), base (0.25mmol), KI (0.5 mmol), K4Fe(CN)6 (0.2 mmol) and DMF (2.5 mL) were added and the mixture was vigorously stirredat 130 C for 8 h under a dry nitrogen atmosphere. Aftercompletion (as monitored by TLC with EtOAc and nhexane),H2O was added and the organic layer was extractedwith EtOAc, washed with brine, dried over MgSO4, filteredand evaporated under reduced pressure. The residue waspurified by column chromatography. The purity of the compoundswas checked by 1H NMR and yields are based onaryl bromide. All the products are known and the spectroscopicdata (FT-IR and NMR) and melting points were consistentwith those reported in the literature [3-8].

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; Sajadi, S. Mohammad; Maham, Mehdi; Letters in Organic Chemistry; vol. 11; 2; (2014); p. 136 – 140;,
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Synthetic Route 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.

To a solution of an appropriate amount of an organic solvent (a mixture of N, N-dimethylformamide (DMF) and polyethylene glycol 200 (PEG-200) in a volume ratio of 4: 1)100 mmol of the compound of the above formula (I), 60 mmol of the compound of the above formula (II), 8 mmol of catalyst bis (triphenylphosphine) cyclopentadienyl ruthenium chloride, 120 mmol of an oxidizing agent bis (trifluoroacetic acid) iodobenzene (PhI (TFA) 2),15 mmol of organic ligands L1, 80 mmol of base, 5,7-triazabicyclo [4.4.0] dec-5-ene (TBD) and 8 mmol of activator of niobium pentachloride were added and then stirred to a temperature of 80 C, The reaction was stirred at this temperature for 11 hours;After completion of the reaction, the reaction system is naturally cooled to room temperature and the pH is adjusted to neutral, filtered and the filtrate is saturated Washed with brine and extracted with ethyl acetate 2-3 times. The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was passed through Silica gel column chromatography eluting with a 1: 2 by volume mixture of chloroform and petroleum ether to give a compound of the above formula (III) The yield was 89.7%.

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; Huang Cheng; Bu Gonggaofamingren; (11 pag.)CN106278838; (2017); A;,
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Synthetic Route of 348-57-2,Some common heterocyclic compound, 348-57-2, name is 1-Bromo-2,4-difluorobenzene, molecular formula is C6H3BrF2, 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.

1-(5-Bromo-2,4-difluorophenyl)ethanone A mixture of AlCl3 (1040 g, 7878.7 mmol) in 1-bromo-2,4-difluorobenzene ([CAS 348-57-2], 600 g, 3108.9 mmol) was stirred for 10 min at 60¡ã C. Acetyl chloride [CAS 75-36-5], 366 g, 4662.4 mmol) was added dropwise in the reaction mixture for 4 h at 60¡ã C. The mixture was stirred an additional 6 h at 95¡ã C. The reaction mixture was cooled to -10¡ã C. Ice (2450 g) was added for 1.5 h. HCl (12 N, 1500 mL) was added and the mixture was stirred for 1 h. EtOAc (9000 mL) was added and the organic layer was washed with water, dried over Na2SO4 and filtered. After concentration, the residue was purified by column chromatography over silica gel (eluent: petroleum ether/EtOAc, 50/1) to yield I-18 (300 g, 41percent).

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

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; Cid-Nunez, Jose Maria; Trabanco-Suarez, Andres Avelino; Vega Ramiro, Juan Antonio; Oehlrich, Daniel; Tresadern, Gary John; Macdonald, Gregor James; US2013/252952; (2013); A1;,
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