Month: January 2021

Related Products of 630-17-1, These common heterocyclic compound, 630-17-1, name is 1-Bromo-2,2-dimethylpropane, 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.

General procedure: A 10 mL Schlenk tube was charged with CoBr2 (6.6 mg, 0.03mmol), 1,3-diisopropyl-1H-benzimidazol-3-ium bromide (L4; 8.5mg, 0.03 mmol), 4-methoxy-N-[(1E)-1-phenylethylidene]aniline(1a, 67.6 mg, 0.30 mmol), 1-chlorooctane (2a, 76.5 muL, 0.45 mmol), and THF (0.69 mL). A 1.92 M solution of t-BuCH2MgBr inTHF (0.31 mL, 0.60 mmol) was added dropwise at 0 C, and themixture was stirred at r.t. for 6 h. The reaction was quenched by theaddition of 3 M aq HCl (1.0 mL), and the mixture was stirred at r.t.for 1 h, then extracted with EtOAc (3 ¡Á 10 mL). The organic layerswere combined, dried (MgSO4), and concentrated under reduced pressure. The crude product was purified by chromatography [silicagel, hexane-EtOAc (40:1)].

Statistics shows that 1-Bromo-2,2-dimethylpropane is playing an increasingly important role. we look forward to future research findings about 630-17-1.

Reference:
Article; Gao, Ke; Yamakawa, Takeshi; Yoshikai, Naohiko; Synthesis; vol. 46; 15; (2014); p. 2024 – 2039;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 25462-61-7, These common heterocyclic compound, 25462-61-7, name is 2,5-Dibromobenzene-1,4-diamine, 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.

In a Schlenk flask, 2,5-dibromo-1,4-phenylenediamine (500 mg, 1.88 mmol) and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yI)-5-hexylthiophene 13 (2.21 g, 7.52 mmol)were charged under the protection of nitrogen. After adding 25 ml toluene, 10 mlethanol and 10 ml Cs2CO3 aqueous solution (2.0 mo/l), the mixture was degassedfor 30 mm. Pd(PPh3)4 (217.3 mg, 18.8 mmol) was added, then the mixture washeated to 80 C and stirred overnight. The reactant was poured into brine andextracted by dichloromethane for several times. The organic phase was dried overMg2504 and the solvent was evaporated in vacuo. The product was purified bychromatography on silica gel (petroleum ether/CH2CI2=1) to give product 14 asyellow flaky crystal (550 mg, 66%). 1H NMR (400 MHz, CDCI3, ppm): 0.90 (t, J = 7.02Hz, 6H), 1.46-1.23 (m, 12H), 1.76-1.64 (m, 4H), 2.82 (t, J = 7.65 Hz, 4H), 3.70 (br,4H), 6.79-6.73 (m, 4H), 7.02 (d, J 3.48 Hz, 2H). m/z[M+HJ calcd for C26H37N2S2441.2399; HR-ESI observed 441.2393. 13C NMR (100 MHz, CDCl3, ppm): 149.5,146.0, 133.3, 129.4, 128.9, 128.4, 122.2, 112.9, 32.0, 31.9, 30.7, 29.1, 22.8, 14.3.

The synthetic route of 25462-61-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; ZHANG, Fan; WANG, Xinyang; TANG, Ruizhi; FU, Yubin; ZHUANG, Xiaodong; FENG, Xinliang; WU, Dongqing; WO2015/43722; (2015); 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. 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C10H13Br

It was prepared as outlined in Scheme 1. In an oven-dried 50 mL round bottom flask under an atmosphere of anhydrous argon, THF (10 mL) was added followed by 1-bromo-3-tert-butylbenzene (5.00 mmol, 1.07 g). This clear, colourless solution was cooled to -90 ¡ãC using a Juablo cooler with a cold finger and an isopropanol bath in an appropriate sized Dewar. This solution was stirred at this temperature for 15 min to ensure it was sufficiently cold. Butyl lithium (3.44 mL, 1.60 M in hexanes) was added dropwise at -90 ¡ãC over 20 min. The resulting clear light yellow solution was stirred for 15 min at -90 ¡ãC. N-Methoxy-N-methyl-2-chloro-2,2-difluoroacetamide (5) (5.50 mmol, 1.00 g), described below, was dissolved in anhydrous THF (4 mL) then added dropwise to the cooled solution of the 1-lithium 3-tert-butylphenyl intermediate over 15 min. The resulting solution was stirred at -90 ¡ãC for 30 min then warmed to room temperature by removing the reaction flask from the cooling bath. The resulting reaction mixture was stirred for 16 h at room temperature then quenched with 1 M HCl (20 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (3 * 10 mL). The combined organic layers were dried over Na2SO4, gravity filtered and concentrated in vacuo. The crude viscous clear liquid was purified by flash chromatography on silica gel (10percent ethyl acetate/90percent hexanes, Rf: 0.40) to yield the desired product as a clear, colourless liquid (0.629 g, 51percent). 1H NMR (CDCl3): d1.37 (s, 9H), 7.46 (t, J = 7.9 Hz,1H), 7.71?7.75 (m, 1H), 7.92?7.95 (m, 1H), 8.16 (br s, 1H) (SupplementaryFig. S19). 13C NMR (CDCl3): d 31.1, 35.0, 120.3 (t, JC,F = 305.1 Hz), 127.5, 127.8 (t, JC,F = 3.2 Hz), 128.6, 129.2, 132.5, 152.2, 181.5 (t, JC,F = 28.2 Hz) (Supplementary Fig. S20). IR (Neat):3410 (w), 3072 (m), 2964 (s), 2871 (s), 1713 (s), 1599 (s), 1579(s), 1367(s), 1162 (s) cm1 (Supplementary Fig. S21). LRMS m/z:248 (M+2, 2percent), 247 (M+1, 1percent), 246 (M+, 5percent), 233 (17percent), 231 (50percent), 203 (22percent), 162 (13percent), 161 (100percent), 145 (11percent), 118 (12percent), 117(10percent), 115 (10percent), 91 (11percent) (Supplementary Fig. S22). HRMS (ESI): MNa+ found 269.0524, calcd for C12H13ClF2ONa+ = 269.0515 (SupplementaryFig. S23). HPLC: Retention time 2.33 min; purity98percent (Supplementary Fig. S24).

The synthetic route of 3972-64-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jollymore-Hughes, Courtney T.; Pottie, Ian R.; Martin, Earl; Rosenberry, Terrone L.; Darvesh, Sultan; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5270 – 5279;,
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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. 7073-94-1, name is 1-Bromo-2-isopropylbenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H11Br

n-Butyl lithium (1.45 mL, 3.63 mmol, 2.5 M in hexane) was added dropwise to a solution of 1-bromo-2-isopropylbenzene (678 mg, 3.41 mmol) in dry diethyl ether (10 mL) at 0 C. The colorless solution was warmed to room temperature and stirred for 3 h. Then, the solution was added dropwise to a dry diethyl ether (5 mL) solution of compound B (434 mg, 1.14 mmol) at -78 C. The yellow solution was warmed to room temperature and stirred for 30 min. The color turned to red. The reaction was followed by TLC and then quenched with NH4Cl (aq) at 0 C. The organic phase was separated and reserved. The aqueous phase was extracted with diethyl ether (3 ¡Á 30 mL). The combined organic phases were washed with water (2 ¡Á 30 mL) and brine (1 ¡Á 30 mL). The organic phase was dried over Na2SO4. The solvent was distilled off by rotary evaporation. The crude product was purified by flash column chromatography on silica gel using hexane/diethyl ether (20/1) as eluent. The product was isolated as a yellow solid (120 mg, yield: 88%). 1H NMR (400 MHz, CDCl3, 25 C): 0.96 (9H, CH(CH3)2), 0.98 (3H, d, J = 6.8 Hz, CH(CH3)2), 1.05 (6H, d, J = 6.8 Hz, CH(CH3)2), 2.89 (2H, sept, CH(CH3)2), 3.02 (1H, sept, CH(CH3)2), 4.19 (1H, br, NH), 5.52 (1H, s, NCH), 6.96 (2H, m, Ar-H), 7.07 (3H, s, Ar-H), 7.11 (1H, d, J = 1.2 Hz, Ar-H), 7.21 (1H, m, Ar-H), 7.28-7.39 (3H, m, Ar-H), 7.37 (1H, d, J = 7.6 Hz, Py-H), 7.57-7.64 (3H, m, Ar-H), 7.68-7.71 (1H, m, Ar-H), 8.97 (1H, s, indole-NH). 13C NMR (100.62 MHz, CDCl3, 25 C): delta = 23.97, 24.01, 24.05, 24.30, 28.00, 28.82, 66.18, 100.43, 111.54, 117.97, 119.74, 120.26, 121.33, 123.27, 123.63, 123.71, 125.81, 126.17, 127.47, 127.72, 129.31, 136.45, 136.87, 137.30, 139.43, 137.30, 139.43, 142.56, 142.96, 146.56, 149.53, and 162.48.

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; Li, Gang; Lamberti, Marina; Mazzeo, Mina; Pappalardo, Daniela; Pellecchia, Claudio; Journal of Molecular Catalysis A: Chemical; vol. 370; (2013); p. 28 – 34;,
Bromide – Wikipedia,
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Electric Literature of 33070-32-5, 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. 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, This compound has unique chemical properties. The synthetic route is as follows.

Preparation 29 4-(2,2-difluoro-13-benzodioxol-5-yl)-2-fluoroaniline A solution of 5-bromo-2,2-difluoro-1,3-benzodioxole (1.73 mmol), bis(pinacolato)diboron (1.90 mmol), potassium acetate (5.20 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)¡¤dichloromethane adduct (0.32 mmol) in N,N-dimethylformamide (8.0 mL) was heated at 80 C. for 2 h. The reaction mixture was cooled and was treated with 2-fluoro-4-iodoaniline (0.86 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)¡¤dichloromethane adduct (0.32 mmol), cesium carbonate (8.65 mmol), and water (2.0 mL). The reaction mixture was then heated at 100 C. for 18 h. The reaction mixture was cooled, poured into brine (60 mL), and extracted with (3*50 mL) ethyl acetate. The combined organic layers were dried over magnesium sulfate and decolorizing charcoal, filtered through Celite, and concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC and neutralization of the collected fractions afforded the title product as a tan solid (70%). ESMS [M+H]+: 267.8.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-2,2-difluorobenzodioxole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; CYTOKINETICS; US2007/259951; (2007); A1;,
Bromide – Wikipedia,
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Synthetic Route of 86845-27-4, 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 86845-27-4 as follows.

(44-1) After N-bromosuccinimide (1.49 g, 6.63 mmol) and 2,2′-azobis(isbutyronitrile) (20 mg) were added to a solution of 4-bromo-1-methyl-2-(trifluoromethyl)benzene (2.0 g, 8.4 mmol) in carbon tetrachloride (20 ml), the mixture was heated under reflux for 5 hours. The temperature of the reaction mixture was returned to room temperature and the residue obtained by removing the solvent under reduced pressure was subjected to silica gel column chromatography (eluding solvent: n-hexane) to give crude 4-bromo-1-bromomethyl-2-(trifluoromethyl)benzene.

According to the analysis of related databases, 86845-27-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP1806332; (2007); 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. 586-61-8, name is 1-Bromo-4-isopropylbenzene, A new synthetic method of this compound is introduced below., Product Details of 586-61-8

Under nitrogen conditions, o-aminobiphenyl (10.0 g, 59 l) was added to the reaction vessel,1-bromo-4′-isopropylbenzene (11.77 g, 59.1 mmol), tris (dibenzylideneacetone) dipalladium (0 ¡¤ lg), tri-tert-butylphosphine (15%, 0.3 g) (1.8 g) and toluene (300 mL) at 60 C for 12 hours. After the reaction solution was cooled, the silica gel filter was filtered and the solution was concentrated and subjected to column chromatography after dichloromethane and hexane to give Compound F-18 (11.50 g, yield 68%).

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; Jilin Aolaide Optoelectric Materials Co., Ltd.; Qin Cuiying; Yu Danyang; Sun Feng; He Jinxin; Wang Shikai; Jin Furong; (19 pag.)CN107162916; (2017); A;,
Bromide – Wikipedia,
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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. 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-N,N-dimethylaniline

a) Synthesis of2-(bis(3-(dimethylamino)phenyl)(hydroxy)methyl)phenol Phenyllithium (2 M in cyclohexane, 9.86 mL, 19.7 mmol) was added during 15 min to a solution of methyl salicylate (3.00 g, 19.7 mmol) in tetrahydrofuran (THF, 20 mL) at -78¡ãC. After stirring for 5 min at -78¡ãC, the reaction mixture was transferred during 20 min to a Grignard reagent prepared from 3-bromo-N,N-dimethylaniline (7.89 g, 39.4 mmol) and magnesium turnings (1.15 g, 47.3 mmol) in THF (ca. l lO mL), which was maintained at 0¡ãC during the addition. The reaction mixture was left warming to room temperature. After stirring at room temperature for 24 h, the reaction mixture was decanted and quenched with a saturated solution of ammonium chloride (ca. 200 mL). Extraction with ethyl acetate, drying (Na2S04) and concentrating gave 7.97 g of the crude product. Column chromatography (Si02, heptane/ethyl acetate 3: 1) finally yielded 2.15 g (30percent) of the target compound. 1H-NMR: 7.20-7.12 (m, 3 H), 6.88-6.84 (m, 1 H), 6.74-6.70 (m, 1 H), 6.70-6.65 (m, 4 H), 6.64-6.60 (m, 1 H), 6.53-6.48 (m, 2 H), 3.70 (br. s, 1 H), 2.84 (s, 12 H). 13C-NMR: 156.25, 150.35, 145.92, 130.37, 130.18, 129.23, 128.60, 118.77, 117.30, 116.58, 112.36, 112.01, 85.01, 40.59.

The synthetic route of 16518-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FIRMENICH SA; HERRMANN, Andreas; (36 pag.)WO2016/116420; (2016); A1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 3814-30-0, name is (Bromomethyl)cyclopentane, 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 3814-30-0, Quality Control of (Bromomethyl)cyclopentane

Example 113A Di-tert-butyl {2-[6-(cyclopentylmethoxy)-1,2-benzoxazol-3-yl]-2-oxoethyl}[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]malonate To a mixture of 150 mg (0.27 mmol) of the compound from Example 99A in 1.5 ml of acetonitrile were added at RT 110 mg (0.80 mmol) of potassium carbonate and 130 mg (0.80 mmol) of (bromomethyl)cyclopentane. The mixture was stirred under reflux for 4 h. After cooling to RT, the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered and concentrated.

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMAN, Andreas; BROHM, Dirk; JOeRIssEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (120 pag.)US2017/121315; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 2789-89-1, name is 1,2-Bis(4-bromophenyl)ethyne, 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. Recommanded Product: 1,2-Bis(4-bromophenyl)ethyne

Example 125 Preparation of N-phenyl-3,4-di(p-bromophenyl)-1-phenyl-1,2-dihydrobenz[c-1,2]azaphosphinine 1-oxide N-phenyl-3,4-di(p-bromophenyl)-1-phenyl-1,2-dihydrobenz[c-1,2]azaphosphinine 1-oxide (81.9 mg, 87%) as a target compound was obtained under the condition of 110 for 30 hours, by the same reaction as the Example 118 above, except for using 1,2-bis(4-bromophenyl)ethyne (100.8 mg, 0.3 mmol) instead of using 3-hexyne of the Example 118 above. 1H NMR (400 MHz, CDCl3) delta 7.68 (dd, J=7.1 Hz, 12.9 Hz, 2H), 7.51 (dd, J=7.4 Hz, 14.2 Hz, 1H), 7.43 (t, J=7.7 Hz, 1H), 7.38-7.35 (m, 3H), 7.31-7.25 (m, 3H), 7.11-7.06 (m, 3H), 7.01-7.00 (m, 4H), 6.88 (t, J=7.8 Hz, 4H), 6.81 (t, J=7.2 Hz, 1H)

The synthetic route of 1,2-Bis(4-bromophenyl)ethyne has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KNU-INDUSTRY COOPERATION FOUNDATION; Lee, Phil Ho; Park, Young Chul; Jeon, In Cheol; Seo, Jung Min; Seo, Bo Ram; US2015/344506; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary