Tag: M.W=100-200

Application of 55289-36-6,Some common heterocyclic compound, 55289-36-6, name is 3-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.

A solution of triphosgene (2.25 g, 7.58 mmol) in toluene (27 mL), cooled in an ice-water bath, was treated slowly with a solution of 3-bromo-2-methylaniline (3.00 g, 16.1 mmol) and DIEA (5.6 mL, 32.2 mmol) in toluene (5.4 mL). The resulting suspension was stirred at room temperature for 2 h. The precipitate was removed by filtration and washed with EtOAc. The combined filtrates were diluted with EtOAc, washed with brine, dried and concentrated to provide l-bromo-3-isocyanato-2- methylbenzene as a brown oil (3.68 g, 98%). NMR (400 MHz, DMSO-d6) delta 7.49 (dd, J=8.1, 0.9 Hz, 1H), 7.31 (dd, J=7.9, 0.7 Hz, 1H), 7.15 (td, J=8.0, 0.7 Hz, 1H), 2.38 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-2-methylaniline, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; KO, Soo Sung; BATT, Douglas A.; BERTRAND, Myra Beaudoin; DELUCCA, George V.; LANGEVINE, Charles M.; LIU, Qingjie; SRIVASTAVA, Anurag S.; WATTERSON, Scott Hunter; WO2014/210087; (2014); A1;,
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Reference of 2270-59-9,Some common heterocyclic compound, 2270-59-9, name is 5-Bromo-2-methylpent-2-ene, molecular formula is C6H11Br, 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 mixture of 5-bromo-2-methylpent-2-ene (0.66 mL, 5.0 mmol) in CH3CN (15 mL) was added 2-hydroxyisoindoline-l,3-dione (3.33 g, 6.0 mmol) and DBU (4.5 mL, 30 mmol) was heated at 1000C for 4 h. Work-up analogous to the procedure described in Example 58 afforded2-(4-methylpent-3-enyloxy)isoindoline-l,3-dione (1.14g, 90%) as a viscous oil.

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-methylpent-2-ene, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/97578; (2009); A1;,
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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. 553-94-6, name is 2,5-Dimethylbromobenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 553-94-6

General procedure: To a flask containing Mg turnings (0.28 g, 14 mmol) was added p-bromotoluene (1.38 g, 8.0 mmol) in THF (8 mL) at room temperature. After being stirred for 2 h, DMF (1.3 mL, 12 mmol) was added to the reaction mixture. The obtained mixture was stirred for 2 h at room temperature. Then, aq NH3 (7 mL, 28-30%) and I2 (4.06 g, 1.6 mmol) were added to the reaction mixture. After being stirred overnight, the reaction mixture was poured into aq sat. Na2SO3 solution and extracted with CHCl3 (3 × 30 mL). The organic layer was dried over Na2SO4 and filtered. After removal of the solvent, the residue was purified by short column chromatography on silica gel (eluent: hexane / ethyl acetate = 9:1, v/v) to provide pure p-tolunitrile (0.77 g) in 67% yield. Most aromatic nitriles mentioned in this work are commercially available and were identified by comparison with the authentic samples.

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 553-94-6.

Reference:
Article; Ishii, Genki; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron Letters; vol. 52; 18; (2011); p. 2404 – 2406;,
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Application of 103-64-0,Some common heterocyclic compound, 103-64-0, name is (2-Bromovinyl)benzene, molecular formula is C8H7Br, 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.

S1: To the appropriate amount of organic solvent DMF, 100 mmol of the compound of the above formula (I), 150 mmol of the compound of the above formula (III), 150 mmol of the amine source cerium ammonium nitrate, 2 mmol of the catalyst dinitrodiammine platinum, 5 mmol of the ligand (3-cyanopropyl) imidazole chloride and 200 mmol sodium hexametaphosphate were added and the temperature was raised to 60 C and the reaction was stirred at that temperature for 8 hours. S1DMF100mmol(I)150mmol(III)150mmol2mmol5mmolL120mmol1,3-(3-)200mmol60C8 Submit CorrectionsCloseS2: After the reaction of step S2 was completed, an aqueous solution of acetic acid having a mass percentage of 20% was added dropwise to the resulting system until the total molar amount of acetic acid added was 200 mmol, and the reaction was stirred at 60 C for 80 minutes. S2S220200mmol60C80 Submit CorrectionsCloseAfter completion of the reaction at step S2, the mixture was poured into ethyl acetate, washed successively with saturated aqueous NaHCO3 and brine, and the aqueous layer was extracted with ethyl acetate. The washed organic layers and the extracted organic layers were combined with anhydrous Na2 SO 4, and the solvent was distilled off under reduced pressure. The residue was purified by flash column chromatography (using n-hexane-ethyl acetate mixture as eluent, volume ratio of 1: 1) to give the compound of the above formula (III) The yield was 95.1%.

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

Reference:
Patent; Shanghai Bokang Fine Chemical Co., Ltd.; Fu Zhiwei; (11 pag.)CN104876871; (2017); B;,
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Electric Literature of 3814-30-0,Some common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, molecular formula is C6H11Br, 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.

N-(4-(ethylsulfonyl)benzyl)-4-(propylamino)benzamide (70 mg, 0.28 mmol) was added sequentially to a 50 mL vial.Bromomethylcyclopentane(45 mg, 0.28 mmol), anhydrous potassium carbonate (115 mg, 0.83 mmol),10 mL of acetonitrile, heated to reflux for 4 hours.The reaction was completed by TLC. Spin the solvent,Wash with saturated brine and dry over anhydrous sodium sulfate.Purification of petroleum ether by column chromatography: ethyl acetate 1:2,Obtained 30mg of white solid,The yield was 23.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Bromomethyl)cyclopentane, its application will become more common.

Reference:
Patent; Fudan University; Wang Yonghui; Qiu Ruomeng; Gong Juwen; Tian Jinlong; Huang Yafei; (65 pag.)CN109206346; (2019); A;,
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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. 460-00-4, name is 1-Bromo-4-fluorobenzene, A new synthetic method of this compound is introduced below., Safety of 1-Bromo-4-fluorobenzene

Synthesis of compound 42C10H7FS M = 178.23 g.mol”1 19F NMR (CDCh 282.5MHz): -109.8 (m, IF, Ar-F).Mass (GC-MS): 133 (41%); 178 (100%)Into a freshly degassed mixture of EtOH (69mL) and H20 (9mL) was added Pd2dba3 (534mg, 0.58mmol, 0.025eq), PCy3 (660mg, 2.35mmol, O.leq), 2-thiophene boronic acid (3.00g, 23.4mmol, leq), K2C03 (6.48g, 46.9mmol, 2eq), and 4- bromofluorobenzene (5.17mL, 47.0mmol, 2eq). The resultant mixture was stirred overnight at 90C and then allowed to reach room temperature. MgS04 was added to quench water and the mixture was filtered on a pad of Celite using ethyl acetate. The filtrate was concentrated and purified on silica gel chromatography (cyclohexane/ ethyl acetate 100:0 to 95:5) to afford compound 42 (3.84g, 92% yield) as a white solid.

The synthetic route of 460-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TFCHEM; DELIENCOURT-GODEFROY, Geraldine; LOPES, Lenaig; WO2012/160218; (2012); A1;,
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Electric Literature 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.

General procedure: Vinyl halide (0.3mmol, if it is solid), CuI (0.0001 mol%, 20 muL in DMSO), PPh3 (2mol%), K2CO3 (0.6mmol), and tetra n-butylammonium acetate were added to a screw-capped test tube with 3 mL of deoxygenated water. The tube was evacuated and backfilled with argon (3 cycles). Under the argon atmosphere, the alkyne (0.4 mmol) and vinyl halide (if it is liquid) were added by syringe at room temperature. The mixture was heated to 100C and stirred for 24 h. After cooling to room temperature, the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.

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

Reference:
Article; Sun, Peng; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng; Tetrahedron; vol. 69; 34; (2013); p. 6969 – 6974;,
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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. 586-61-8, name is 1-Bromo-4-isopropylbenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H11Br

[00312j A mixture of 4-(benzyloxy)aniline (7.8 g, 39.03 mmol), 1-bromo-4- isopropylbenzene (8.5 g, 42.93 mmol), X-Phos (2.3 g, 4.68 mmol), Pd(OAc)2 (0.53 g, 2.34 mmol) and Cs2CO3 (50.9 g, 156.12 mmol) in toluene(150 mL) was purged with N2 and then reflux overnight. The reaction mixture was cooled to RT and filtered. The filtrate was concentrated and purified by silica column chromatography (PE:EA, 20:1) to give 7.1 g (57%) of the title compound. ?H NMR (CDC13, 300 MHz): oe 1.23 (d, J= 6.9 Hz, 6H), 2.77-2.92 (m, 1H), 5.04 (s, 2H), 6.87-6.94 (m, 4H), 7.01-7.04 (m, 2H), 7.08-7.10 (m, 2H), 7.3 1-7.46 (m, 5H). [M+H] Calc?d for C22H23N0, 318; Found, 318.

The synthetic route of 586-61-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; QUANTICEL PHARMACEUTICALS, INC.; BOLOOR, Amogh; KANOUNI, Toufike; STAFFORD, Jeffrey Alan; VEAL, James Marvin; WALLACE, Michael Brennan; (173 pag.)WO2016/44429; (2016); A1;,
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Synthetic Route of 2695-47-8, 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. 2695-47-8, name is 6-Bromo-1-hexene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of 2-(4-bromobutyl)-oxirane (I): A Solution of 3- Chloroperbenzoic acid (55-75% pure, 4.54 g, 18.39 mmol) in 20 ml dichloromethane was added dropwise to a stirred solution of 6-bromo-l-hexne (2g, 12.26 mmol) in 20 ml of dichioromethane. After addition, the mixture was stirred at 25 C for 16h, to precipitate 3-chiorobenzoic acid. Finally the reaction mixture was evaporated to dryness under vacuum, dissolved in ethyl acetate, washed initially with 4% sodium dithionate followed by saturated sodium bicarbonate and water. Finally the organic layer was dried over sodium sulphate, evaporated and dried under vacuo to obtain the final compound (I) with 90% isolated yield. -NMR (400 MHz, CDC13) delta ppm: -NMR (400 MHz, CDC13) delta ppm: 1 .48- 1 .6(6H, m, CH2) 2.47 ( 1 H, d, J = 2.4, OCH) 2.75 (t, J = 4, 1 H, OCHb), 2.91 (bs, 1 H, OCHa) 3.41 (t, J = 6.4, 2H, CH2-Br) .

The synthetic route of 6-Bromo-1-hexene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VYOME BIOSCIENCES PVT. LTD.; SENGUPTA, Shiladitya; CHAWRAI, Suresh Rameshlal; GHOSH, Shamik; GHOSH, Sumana; JAIN, Nilu; SADHASIVAM, Suresh; BUCHTA, Richard; BHATTACHARYYA, Anamika; WO2015/114666; (2015); 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. 766-46-1, name is 2′-Bromophenylacetylene, A new synthetic method of this compound is introduced below., Application In Synthesis of 2′-Bromophenylacetylene

General procedure: To the mixture of phenylacetylene (1 mmol), water (3.0 mL),silver perfluorooctanesulfonate (5 mol%) and perfluorooctane sulfonateacid (2 mol%) was added. The mixture was stirred at 100 Cfor 8 h. The solution was extracted with n-hexane (diethyl ether)(3 5 mL), the combined extract was dried with anhydrous MgSO4. The rest of the solution was used for the next cycle of reaction. Theextraction solvent was removed and the crude product was separatedby column chromatography to give the pure sample.

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; Dong, Qizhi; Li, Ningbo; Qiu, Renhua; Wang, Jinying; Guo, Cancheng; Xu, Xinhua; Journal of Organometallic Chemistry; vol. 799-800; (2015); p. 122 – 127;,
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