Tag: M.W=100-200

Reference of 108-85-0, The chemical industry reduces the impact on the environment during synthesis 108-85-0, name is Bromocyclohexane, I believe this compound will play a more active role in future production and life.

General procedure: To a flame-dried Schlenk tube equipped with a magnetic stir bar was loaded alkyl bromide (0.15 mmol, 100 mol%, solid), halogenated pyridine (0.30 mmol, 300 mol%, solid), ligand (0.015 mmol, 10 mol%), zinc powder (0.45 mmol, 300 mol%). The tube was capped with a rubber septum and moved to a dry glove box, at which NiBr2 (0.015 mmol, 10 mol%), MgCl2 (0.15 mmol, 100 mol%) and Bu4NBr (0.075 mmol, 50 mol%) were added. Then the tube was moved out of the glove box. Alkyl bromide (0.15 mmol, 100 mol%, liquid), halogenated pyridine (0.30 mmol, 300 mol%, liquid), pyridine (0.15 mmol, 100 mol%) and DMA(1.0 mL) were added via syringe. After the reaction mixture was allowed to stir overnight under N2 atmosphere at 30 C, it was directly loaded onto a silica column without work-up. The residue in the reaction vessel was rinsed with small amount of DCM or eluent. Flash column chromatography provided the product as solid or oil.

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, Bromocyclohexane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Huiyan; Liang, Zhuye; Qian, Qun; Lin, Kunhua; Synthetic Communications; vol. 44; 20; (2014); p. 2999 – 3007;,
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Synthetic Route of 1073-06-9, 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. 1073-06-9, name is 1-Bromo-3-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

An argon filled 50 mL two-necked flaskequipped with a stir bar and a gas condenser was charged withmagnesium turnings (129 mg, 5.300 mmol). After three successivevacuum/argon cycles, THF (15 mL) and one grain of iodine wereadded, and the brownish suspensionwas stirred for 15 min at roomtemperature. Subsequently fluorinated bromobenzene(5.200 mmol) was added. An exothermic reaction was followed bychanges of the color of the reaction mixture from original brown,through colorless to final grayish. This suspensionwas stirred 2 h atroom temperature and then 3-phenylisobenzofuran-1(3H)-one(19) (1.000 g, 4.757 mmol) was added and stirring continued for16 h. Then Ac2O (4 mL) was added dropwise and the reactionmixture was refluxed at the temperature of the oil bath 70 C foradditional 30 min. A dense yellowish precipitate was formed. Theyellow suspension was cooled to room temperature, diluted withether (100 mL), and washed with a saturated aqueous solution ofNaHCO3 (3 15 mL). The deep yellow organic phase was dried overMgSO4. Solvents were removed under reduced pressure and columnchromatography on silica gel (hexane/ethyl-acetate – 4:1)afforded products as yellow crystalline solids. 1-(3-Fluorophenyl)-3-phenylisobenzofuran (3) was synthesizedfrom 1-bromo-3-fluorobenzene (14) (581 mL, 5.200 mmol),magnesium (129 mg, 5.300 mmol), and 19 (1.000 g, 4.757mmol) inTHF (15 mL) according to GP1. Compound 3 was obtained as abright yellow crystalline solid (1.216 g, 4.218 mmol, 89%).Mp 130.9e132.0 C. 1H NMR (400 MHz, CDCl3): delta 6.94e7.01 (m,1H), 7.01e7.10 (m, 2H), 7.29e7.35 (m, 1H), 7.40e7.47 (m, 1H),7.47e7.53 (m, 2H), 7.60e7.65 (m, 1H), 7.71e7.74 (m, 1H), 7.80e7.87(m, 2H), 7.93e7.97 (m, 2H). 13C {1H} NMR (125 MHz, CDCl3): delta 111.3(d, JC,F 23.6 Hz), 113.5 (d, JC,F 21.5 Hz), 119.8, 120.2 (d,JC,F 2.8 Hz), 120.3, 122.1, 122.7, 125.0, 125.2, 125.8, 127.2, 129.0,130.5 (d, JC,F 8.6 Hz), 131.3, 133.5 (d, JC,F 8.6 Hz), 142.3 (d,JC,F 3.2 Hz), 144.4, 163.3 (d, JC,F 245.1 Hz). 19F NMR (470 MHz,CDCl3): delta 108.92 (ddd, 1JF,H 10.3 Hz, 2JF,H 8.6 Hz, 3JF,H 6.0 Hz,1F). IR (KBr): 3051, 3039, 1625, 1608, 1579, 1543, 1518, 1503, 1491,1458, 1451, 1443, 1414, 1397, 1315, 1274, 1259, 1213, 1194, 1160, 1141,1111, 1096, 1067, 1028, 1007, 994, 963, 951, 902, 877, 860, 854, 838,829, 773, 762, 747, 744, 736, 723, 678, 665, 659, 599, 554, 523,490 cm1. MS, m/z (%): 288.1 (100, M), 270.1 (5), 259.1 (23), 239.1(11), 183.1 (10), 165.1 (9), 144.0 (10). HRMS, (EI) for (C20H13FO):calcd 288.0950, found 288.0948. Anal. Calcd. for C20H13FO: C, 83.32;H, 4.54. Found: C, 83.01; H, 4.45.

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-3-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kaleta, Ji?i; ?imkova, Ludmila; Li?ka, Alan; Bim, Daniel; Madridejos, Jenica M.L.; Pohl; Ruli?ek, Lubomir; Michl; Ludvik, Ji?i; Electrochimica Acta; vol. 321; (2019);,
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Synthetic Route of 55289-36-6, 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. 55289-36-6, name is 3-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: 2-methylbiphenyl-3-amine A mixture of 3-bromo-2-methylaniline (Aldrich, cat#530018: 0.39 mL, 3.2 mmol), phenylboronic acid (Aldrich, cat#P20009: 0.50 g, 4.1 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Aldrich, cat#697230: 0.13 g, 0.16 mmol) and potassium carbonate (1.32 g, 9.57 mmol) in 1,4-dioxane (20.0 mL) and water (7 mL) was sparged with nitrogen for 5 min. The mixture was then heated and stirred at 110 C. for 1.5 h. The reaction mixture was cooled to room temperature, quenched with saturated aqueous NaHCO3, and extracted with ethyl acetate (3*10 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column eluting with ethyl acetate in hexanes (0?15%) to afford the desired product. LC-MS calculated for C13H14N (M+H)+: m/z=184.1; found 184.1. 1H NMR (400 MHz, DMSO) delta 7.40 (dd, J=7.6, 6.8 Hz, 2H), 7.32 (dd, J=7.6, 7.2 Hz, 1H), 7.29-7.14 (m, 2H), 6.92 (dd, J=7.6, 7.6 Hz, 1H), 6.64 (d, J=7.2 Hz, 1H), 6.40 (d, J=7.2 Hz, 1H), 4.89 (s, 2H), 1.92 (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, 3-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Incyte Corporation; Lajkiewicz, Neil; Wu, Liangxing; Yao, Wenqing; (58 pag.)US2017/174679; (2017); A1;,
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These common heterocyclic compound, 7051-34-5, name is (Bromomethyl)cyclopropane, 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. Product Details of 7051-34-5

[>^CO2Et[1,3] Dithiane-2-carboxylic acid ethyl ester (1.29 g, 6.71 mmol) and bromomethyl-cyclopropane (0.99 g, 7.38 mmol) dissolved in dry DMF (1 mL), was added slowly to a stirred suspension of NaH (60 % in mineral oil, 268 mg, 6.71 mmol) in dry toluene (2 mL). The mixture was stirred at room temperature overnight and LC-MS showed completion of the reaction. The reaction was quenched with H2O, diluted with EtOAc. The organic layers were washed with H2O and dried with MgSO^ The solution was filtered and concentrated in vacuo to give desired product, 2-cyclopropylmethyl-[l,3]dithiane-2-carboxyIic acid ethyl ester, as yellow oil (1.49 g, 91%). LC-MS (ESI+): m/e = 247.0 [M+l]+ (exact ms: 246.07).

The synthetic route of (Bromomethyl)cyclopropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANADYS PHARMACEUTICALS, INC.; WO2008/82725; (2008); A1;,
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Electric Literature of 10269-01-9, A common heterocyclic compound, 10269-01-9, name is (3-Bromophenyl)methanamine, molecular formula is C7H8BrN, 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: (c) A solution of Boc2O (1.29g, 5.91mmol) in CH2Cl2 (10ml) was added to a suspension of 4-bromobenzylamine (1.00g, 5.38mmol) and Et3N (0.60g, 5.91mmol) in CH2Cl2 (10ml) for 5min at 0C with a CaCl2 tube. The reaction mixture was stirred overnight at room temperature. Then, H2O (50ml) was added to the mixture, and the organic layer was separated. The aqueous layer was extracted with CHCl3 (50ml×3). The combined organic layer was washed with H2O (50ml×1) and then brine (50ml×1), dried over Na2SO4 (anhyd), filtered, and concentrated under reduced pressure to afford (4-bromobenzyl)carbamic acid tert-butyl ester (1.63g, quant. y.) as a colorless solid.

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; Tashima, Toshihiko; Murata, Hiroaki; Kodama, Hidehiko; Bioorganic and Medicinal Chemistry; vol. 22; 14; (2014); p. 3720 – 3731;,
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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. 399-94-0, name is 1-Bromo-2,5-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 399-94-0

A tetrahydrofuran (30 ml) solution of 1-bromo-2,5-difluorobenzene (1.08 ml, 9.60 mmol) was stirred at -78C, followed by the addition of a hexane solution (7.32 ml, 11.5 mmol) of n-butyl lithium. To the reaction mixture was added a tetrahydrofuran (10 ml) solution of 4-pyridinecarboxyaldehyde(0.764 ml, 8.00 mmol) at -78C. The resulting mixture was stirred at the same temperature for 30 minutes. After the temperature of the reaction mixture was raised to room temperature, diethyl ether was added thereto. The resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography. The fraction obtained from the hexane:ethyl acetate=7:3 eluate was concentrated under reduced pressure. The solid thus obtained was washed with diisopropyl ether and then collected by filtration to give the title compound (1.15 g, 5.20 mmol, 65%) as a white powder. 1H-NMR (400MHz, CDCl3) delta: 4.25 (1H,brs), 6.09 (1H,s), 6.89-7.05(2H,m), 7.14-7.23 (1H,m), 7.34 (2H,d, J=5.4Hz), 8.44(2H,d,J=5.4Hz).

According to the analysis of related databases, 399-94-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1640366; (2006); A1;,
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Synthetic Route of 7745-91-7, These common heterocyclic compound, 7745-91-7, name is 3-Bromo-4-methylaniline, 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.

450 mL of water, 50.0 g (0.268 mol) of 2-bromo-p-toluidine,100 mL (1.102 mol) of concentrated hydrochloric acid was added and heated to 90 C. with stirring.Subsequently, the mixture was stirred at the same temperature for 1 hour, then cooled to room temperature, and further cooled to -10 C. with an ice water bath. Next, an aqueous solution prepared by dissolving 22.3 g (0.323 mol) of sodium nitrite in 70 mL of water was added dropwise at a temperature not exceeding 5 C., followed by stirring at 5 C. or lower for 30 minutes, filtration with an aid, diazonium An aqueous solution of salt was obtained.Next, 67.0 g (0.403 mol) of potassium iodide (Wako Pure Chemical Industries, Ltd.) and 230 mL of water were added to a 1 L four-necked round bottom flask equipped with a stirrer, Erlin condenser, 1 L dropping funnel and thermometer The mixture was placed in a water bath and stirred at 10 C. Next, after the aqueous solution of the diazonium salt was dropped, the water bath was removed to return to room temperature, the temperature was further increased to 40 C., and the mixture was stirred for 4 hours. The obtained reaction solution was returned to room temperature again, 300 mL of DCM was added and the mixture was transferred to a 2 L separatory funnel, then the aqueous layer was separated and extracted with 250 mL of DCM. Next, the DCM layers were combined, washed with 250 mL of 20% sodium thiosulfate aqueous solution, 250 mL of saturated aqueous multilayer water, three times with 250 mL of water, dried with magnesium sulfate, then removed by suction filtration of magnesium sulfate, The solvent was distilled off under reduced pressure. Subsequently, the resulting crude oil was purified by silica gel column chromatography using n-heptane as a developing solvent to obtain 73.5 g (yield 92.2%) of the desired iodide.

Statistics shows that 3-Bromo-4-methylaniline is playing an increasingly important role. we look forward to future research findings about 7745-91-7.

Reference:
Patent; YAMAGATA UNIVERSITY; CHEMIPRO KASEI KAISHA LIMITED; KIDO, JUNJI; SASABE, HISAHIRO; TAKAHASHI, JUN; NAGAI, NAGAI; (723 pag.)JP2018/90561; (2018); A;,
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Related Products of 114078-88-5,Some common heterocyclic compound, 114078-88-5, name is 5-Bromo-1,2,3-triazine, molecular formula is C3H2BrN3, 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.

Using the most conditional verification experiment, the reaction steps are: in a 10mL dry sealed reaction tube, add 5-bromo-1,2,3-triazine 1a (15.9mg, 0.10mmol), DBN (37.3 mg, 0.30 mmol) and diethyl cyanomethyl phosphate 1b (35.4 mg, 0.20 mmol). After nitrogen substitution three times, the solvent 1,4-dioxane (1.0 mL) was added, and the sealed reaction tube was placed at 70 C to react. The reaction was monitored by TLC. After the reaction was completed, it was extracted with dichloromethane (3 * 10mL). The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. After column chromatography, the target product 1c (24.6mg) was obtained. 80%.

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-1,2,3-triazine, its application will become more common.

Reference:
Patent; Chongqing University; Li Baosheng; Luo Han; Zhang Yuan; An Jiaoyu; Xu Mingchuan; Lu Qixing; Tang Zongyuan; Li Shanshan; (16 pag.)CN111004284; (2020); 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. 1647-26-3, name is 1-Bromo-2-cyclohexylethane, A new synthetic method of this compound is introduced below., SDS of cas: 1647-26-3

solution of tert-butyl {6-[({[(Z)-(4-methyl-5-oxo-4,5-dihydro-1 ,2,4-oxadiazol-3- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (100 mg, 0.235 mmol, 1 eq.) in A/,/V-dimethylformamide (2 ml) was treated with sodium hydride (10 mg, 0.259 mmol, 1.1 eq.) and stirred at room temperature for 30 minutes. (2-Bromoethyl)cyclohexane (67 mg, 0.353 mmol, 1.5 eq.) was then added and stirring was allowed overnight. The reaction was quenched by addition of water and extracted with EtOAc (3 x 20 ml). The organics were combined, washed with aq. sat. NaCI. dried over gSO and concentrated to afford tert-butyl (2- cyclohexylethyl ){6-[({[(Z)-(4-methyl-5-oxo-4 , 5-d i hyd ro- 1 ,2 ,4-oxad iazol-3- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (108 mg, 86% yield) which was used in the next step without further purification.

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; BAYER INTELLECTUAL PROPERTY GmbH; BRAUN, Christoph; SAWADA, Haruko; LACHAISE, Helene; BRUNET, Stephane; RINOLFI, Philippe; DUBOST, Christophe; COQUERON, Pierre-Yves; MAECHLING, Simon; REBSTOCK, Anne-Sophie; WACHENDORFF-NEUMANN, Ulrike; WO2013/37717; (2013); A1;,
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These common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, 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. Quality Control of 1-Bromo-2-cyclohexylethane

To a solution of 1.22 g of 2-cyclohexylethyl bromide and 1.56 g ethyl N-[7-chloro-3-[2,3-O-(1-methylethylidene)-5-O-(2H-tetrahydropyran-2-yl)-beta-D-ribofuranosyl]-3H-imidazo[4,5-b]-pyridin-5-yl]-carbamate in 15 ml of dry dimethylformamide is added 0.25 g of sodium hydride (60% dispersion in mineral oil). After a few minutes the gas evolution subsides and the mixture is heated to 70 for 20 minutes. The reaction is quenched with water, and extracted three times with ethyl acetate. The organic extract is washed with water and dried (sodium sulfate). Evaporation of the solvent in vacuo gives an oil which is purified by flash chromatography on silica gel (40% ether/hexane followed by ether) to give ethyl N-[7-chloro-3-[2,3-O-(1-methylethylidene)-5-O-(2H-tetrahydropyran-2-yl)-beta-D-ribofuranosyl]-3H-imidazo[4,5-b]pyridin-5-yl]-N-(2-cyclohexylethyl)-carbamate.

The synthetic route of 1-Bromo-2-cyclohexylethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4977144; (1990); A;,
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