Author: Jessica.F

Electric Literature of 32863-30-2,Some common heterocyclic compound, 32863-30-2, name is 4-(Bromomethyl)benzo[c][1,2,5]oxadiazole, molecular formula is C7H5BrN2O, 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.

4-bromomethylbenzimidazolium chloride (19. 7 g, 0.1 mol),DMSO 15 ml,Sodium bicarbonate (10 g, 0.12 mol) was added to the reaction flask. Heating to 100-150 C under nitrogen. After completion of the reaction, the mixture was cooled to room temperature and extracted with water and ethyl acetate. The organic layers were combined and washed with saturated brine. Dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give 10. 6 g of a pale yellow solid in 71.6% yield, mp 108-109 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Bromomethyl)benzo[c][1,2,5]oxadiazole, its application will become more common.

Reference:
Patent; Hefei Huafang Pharmaceutical Science & Technology Co., Ltd,; HE, YONG; WU, ZONGHAO; CHEN, SHIYUN; LI, JIAJIA; GAO, YONGHAO; (6 pag.)CN102285978; (2016); B;,
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Reference of 707-34-6, 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. 707-34-6, name is 1,3,5-Tribromoadamantane, This compound has unique chemical properties. The synthetic route is as follows.

A 250 ml three-necked flask equipped with a condenser was charged with 3.7 g (10 mmol) of 1,3,5-tribromoadamantane, 16.0 g of 1,3-dibromo-2-methoxybenzene (60.0 mmol) and30 ml of 1,2-dichloroethane,Condenser duct from the upper end connected to an inverted funnel 30% NaOH aqueous solution,To absorb the HBr produced by the reaction.At 0 ice water bath,1.0 g (ie, 4.0 mmol) of AlBr3 was added to the reaction system,Continue stirring in the ice water bath for half an hour,Then gradually returned to room temperature,The reaction system was heated in an oil bath to 60 C for 5 hours,The reaction solution was cooled to room temperature,Pour into 100 mL of acidic ice water and stir for 1 h.After the ice has completely melted, 100 ml of methylene chloride 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 mixture is then recrystallized from a mixed solution of ethyl acetate and methanol ,6.58 g of a white solid was obtained in a yield of 71%.

The chemical industry reduces the impact on the environment during synthesis 1,3,5-Tribromoadamantane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chinese Academy Of Sciences Physics And Chemistry Technology Institute; Chen Jinping; Li Yi; Yu Tianjun; Zeng Yi; (18 pag.)CN107266319; (2017); 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. 5401-62-7, name is 1,2-Dibromocyclohexane, A new synthetic method of this compound is introduced below., Recommanded Product: 5401-62-7

General procedure: To a stirred solution of bisphenol (5/12) (1 mmol) in MeCN (15 mL) was added K2CO3 (5 mmol) and theresultant suspension was stirred for 30 min. Then, 1,6-dibromohexane (3 mmol) was added dropwise overa period of 10 min. Further, the crude reaction mixture was stirred for 12 h at reflux. At the conclusion ofthe reaction (TLC monitoring), the crude mixture was filtered through celite pad (washed with CH2Cl2)and concentrated under reduced pressure. The crude product was purified by column chromatography.Cyclophane products (7 and 18) data obtained by this procedure was compared with data obtained byhydrogenation process.

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; Kotha, Sambasivarao; Waghule, Gopalkrushna T.; Heterocycles; vol. 90; 2; (2015); p. 1289 – 1298;,
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These common heterocyclic compound, 60956-23-2, name is 1,2-Dibromo-4-methylbenzene, 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. Safety of 1,2-Dibromo-4-methylbenzene

General procedure: A 12 mL vial was charged with [Pd(cinnamyl)Cl]2(1,5 mol%), dppp (3 mol%). and a stirring bar. Then, 1,2-dibromo-benzene(0.5 mmol), DBU (4.0 eq) and toluene (3 mL) were injected by syringe underargon. The vial (or several vials) was placed in an alloy plate, which wastransferred into a 300 mL autoclave of the 4560 series from Parr Instrumentsunder argon atmosphere. After flushing the autoclave three times with CO, apressure of 10 bar of CO was adjusted at ambient temperature. Then, thereaction was performed for 16-24 h at 140 oC. After the reactioncompleted, the autoclave was cooled down with ice water to room temperature andthe pressure was released carefully. After evaporation of the organic solventthe residue was adsorbed on silica gel and the crude product was purified bycolumn chromatography using EA/pentane(1:1) for phthalimides and MeOH/EA (1:40) for the amides as eluent.

The synthetic route of 1,2-Dibromo-4-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Jianbin; Natte, Kishore; Wu, Xiao-Feng; Tetrahedron Letters; vol. 56; 2; (2015); p. 342 – 345;,
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41825-73-4, name is 2-Bromo-4,6-dimethylaniline, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C8H10BrN

In 100mL Schlenk flask 2-bromo-4,6-dimethyl aniline (manufactured by Kanto Chemical Co., Inc.) (4.97g, 24.9mmol) and di-tert-butyl dicarbonate (manufactured by Kanto Chemical Co., Inc.) (13.6g, 62.1mmol) They were weighed, and dissolved by adding dehydrated toluene (manufactured by Kanto Chemical Co., Inc.) (35 mL). Introducing a reaction vessel in an oil bath preset at 90 C., and reacted for 33 hours. After completion of the reaction, the solvent was removed by silica column chromatography (hexane: ethyl acetate = 20: 1) as a white solid (2-bromo-4,6-dimethylphenyl) – carbamic acid tert-butyl ester was isolated ( 5.10g, 17.0mmol, 68%).

The synthetic route of 41825-73-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tokyo Institute of Technology; JapanPolychemCo., Ltd.; Osakada, Kotaro; Takeuchi, Daisuke; Takano, Shigenaga; Uchino, Hideshi; Kobayashi, Minoru; (93 pag.)JP2015/117237; (2015); A;,
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Electric Literature of 1177559-63-5, 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 1177559-63-5 as follows.

To a stirred solution of (3-bromo-2-fluorophenyl)methanamine hydrochloride (15.0 g, 62.5 mmol, 1 equiv) and 1 ,1 -dimethoxypropan-2-one (9.58 g, 81 .25 mmol, 1 .3 equiv) in DCE (150 mL) was added sodium triacetoxyborohydride (17.22 g, 81 .25 mmol, 1 .3 equiv) at room temperature and the mixture was stirred overnight. 30% aqueous K3P04 (pH=14) was added to the reaction mixture, the layers were partitioned and the aqueous layer was extracted with EtOAc (2 x 200 mL), and the organics were combined and washed with brine ( 100 mL), and dried over Na2S04. The organic solvent was concentrated to give the N-(3- bromo-2-fluorobenzyl)-1 ,1 -dimethoxypropan-2-amine as a colorless liquid (19 g, crude). LC-MS (ES) m/z = 306.2, 308.0 [M+H]+. NMR (400 MHz, DMSO-d6) delta ppm 0.94 (d, J = 6.4 Hz, 3 H), 1 .89 (br.s, 1 H), 2.62 (t, J = 6 Hz, 1 H), 3.22 (s, 3 H), 3.25 (s, 3 H), 3.73 – 3.76 (m, 1 H), 3.80 – 3.84 (m, 1 H), 4.06 (d, J = 5.6 Hz, 1 H), 7.09 (t, J = 8 Hz, 1 H), 7.44 (t, J = 6.8 Hz, 1 H), 7.53(t, J = 7.2 Hz, 1 H).

According to the analysis of related databases, 1177559-63-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AXTEN, Jeffrey; KETHIRI, Raghava Reddy; KRISTAM, Rajendra; VENKATESHAPPA, Chandregowda; (162 pag.)WO2018/15879; (2018); A1;,
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These common heterocyclic compound, 1159977-65-7, name is 6-Bromoimidazo[1,2-b]pyridazine, 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: 1159977-65-7

To a solution of 6-bromoimidazo[1,2-b]pyridazine (1.98 g, 10.0 mmol) in methanol (50 mL) at -10 C. was added N-iodosuccinimide (2.47 g, 11.0 mmol) in portions. The mixture was stirred at -10 C. for 30 minutes and then allowed to warm up to rt. The reaction was continued to stir at rt for 18 hours, and then concentrated in vacuo. The residue was dissolved in 100 mL of DCM and washed with 50 mL of aqueous Na2CO3 solution. The organic phase was concentrated in vacuo to give the title compound as a light yellow solid (2.0 g, 61%). MS (ESI, pos. ion) m/z: 323.9 [M+H]+; 1H NMR (400 MHz, CDCl3): delta 7.83 (s, 1H), 7.78 (d, J=9.4 Hz, 1H), 7.21 (d, J=9.4 Hz, 1H).

The synthetic route of 6-Bromoimidazo[1,2-b]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Calitor Sciences, LLC; Xi, Ning; US2014/134133; (2014); 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. 40422-70-6, name is 1-Bromo-3-(2-bromoethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-3-(2-bromoethyl)benzene

To a 100 ml three neck round bottomed flask under nitrogen atmosphere, (R)-2- isopropyl-3,6-dimethoxy-2,5-dihydropyrazine (4 g, 21.7 mmol) was dissolved in dry THF (28 ml) and cooled to -78 C. To this reaction mixture, 1 .6 M solution of n-BuLi in hexanes (16.3 ml, 26 mmol) was added dropwise at -78 C and stirred for 15 minutes. A solution of l-bromo-3- (2-bromoethyl)benzene (5.73 g, 21 .7 mmol) in dry THF (13 ml) was added dropwise at -78 C and stirred for 1 h followed by stirring at rt for 3 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted using ethyl acetate. The combined organic layer was dried over sodium sulfate and concentrated and purified by flash column purification with 1 -3 % ethyl acetate in hexanes to yield 3.3 g of (2S,5R)-2-(3-bromophenethyl)-5-isopropyl- 3,6-dimethoxy-2,5-dihydropyrazine.

According to the analysis of related databases, 40422-70-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRAMELD Kenneth; OWENS Timothy; WO2015/195950; A1; (2015);,
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Synthetic Route of 117635-21-9, 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 117635-21-9 as follows.

In the dry box the mixture of boronic acid pinacol ester,4, (6.44g, 18.55mmol), 1 ,4-dibromo-2,5-dihexylbenzene (3.75g, 9.27mmol), Aliquat 336 (0.8g), and Pd(PPh3) (0.536g, 0.464mmol) in degassed toluene (l OOmL) was prepared. Outside dry box, the degassed Na2CO3 (2.95g, 27.83mmol in 50 ml_ of water) solution was added to the former mixture under nitrogen, and then the resultant mixture was stirred at 90C for 38hrs. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4. Filtration, concentration of the filtrate, and then the silica column chromatography (0-4% ethyl acetate in hexane) provided the desired product (3.62g, 60% yield) as a white solid. This diboc-protected material was deprotected by the overnight reaction at room temperature with TFA solution (4ml_ of TFA in 30ml_ of DCM). The reaction mixture was concentrated under reduced pressure followed by the neutralization with saturated NaHCO3. Ethyl acetate extraction, drying over anhydrous MgSO4, concentration of the organic layer under reduced pressure, then silica column chromatography (30% ethyl acetate in hexane) provided the desired diamine material,8, (2.5g, 99% yield).

According to the analysis of related databases, 117635-21-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; PARK, Kyung-Ho; RADU, Nora, Sabina; JOHANSSON, Gary, A.; FENNIMORE, Adam; DELANEY, William, J.; LECLOUX, Daniel, David; WO2011/159872; (2011); A1;,
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. 875664-41-8, name is 3-Bromo-4,5-difluoroaniline, A new synthetic method of this compound is introduced below., name: 3-Bromo-4,5-difluoroaniline

This acid (700 mg,2.33mmol), 3-aminobenzonitrile (347.8mg, 2.91 mmol), HATU (1108mg, 2.9l4mmol) andDIPEA (1 .2mL, 6.99 mmol) was dissolved in DMF (7 mL) and the mixture was stirred at roomtemperature for 16 h. The mixture was poured in 100 mL ice water and was extracted withEtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered andconcentrated in vacuo. The residue was purified on a silica using a gradient eluent HeptaneEtOAc 100-0 -> 50-50. The product fractions were collected and concentrated in vacuo. The product was crystallized from 2-propanol, filtered off and dried in vacuo, yielding compound 158 (518 mg) as a white solid.Compound 205 (893 mg) was prepared similarly as described for compound 158 using 3-bromo-4,5-difluoroaniline (970 mg, 4.663 mmol) instead of 3-aminobenzonitrile and stirring at 60C during 18 h. The obtained residue was warmed with CH2C12/heptanes and the white solid collected by filtration. Method A: Rt: 1.79 mm mlz: 489.9 (M-H)- Exact mass: 488.98. ?H NMR (400 MHz, DMSO-d6) oe ppm 1.08 (d, J=7.0 Hz, 3 H), 3.84 – 3.99 (m, 1 H), 3.92 (s, 3 H), 7.36 (d,J=1.8 Hz, 1 H), 7.67 (d, J=1.5 Hz, 1 H), 7.80 – 7.93 (m, 2 H), 8.19 (br. s., 1 H), 10.30 (s, 1 H). Differential scanning calorimetry: From 30 to 300 C at 10C/mm: peak at 196.72 C.

The synthetic route of 875664-41-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
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