Month: November 2020

These common heterocyclic compound, 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide, 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. 5003-71-4

Tert-butyl n-(3-bromopropyl)carbamate: Prepared from 3-bromopropylamine hydrobromide and BOC2O in the presence of base in dichloromethane, 9.89 mmol: 1H NMR (CDCl3) delta 5.07 (br, 1H), 3.31 (t, 2H, J=6.6 Hz), 3.12 (apparent br q, 2H, J=6.0 Hz), 1.92 (p, 2H, J=6.6 Hz), 1.30 (s, 9H).

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 5003-71-4.

Reference:
Patent; Borowsky, Beth; Blackburn, Thomas P.; Ogozalek, Kristine; US2003/82623; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

51554-93-9,Some common heterocyclic compound, 51554-93-9, name is 1-Bromo-4-octylbenzene, molecular formula is C14H21Br, 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 hexane solution of n-butyllithium (1.65 M, 40 mL, 66 mmol) was dropwise added to a dewatered THF (400 mL) solution of the compound 3 (by Wako Pure Chemicals, 16.2 g, 60 mmol) at -78 C., and the mixture was reacted for 1 hour. Next, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxabororane (16.8 g, 90 mmol) was added thereto and stirred overnight at room temperature, and then poured into water and extracted with hexane. The organic phase was washed with water, dried with anhydrous sodium sulfate, and then the solvent was evaporated away. The residue was purified through silica gel chromatography (eluent: hexane/ethyl acetate=10/1 (v/v)) and then dried in vacuum to give a colorless oil of the compound 4 (yield: 17.5 g, 92%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-octylbenzene, its application will become more common.

Reference:
Patent; KYUSHU UNIVERSITY NATIONAL UNIVERSITY CORPORATION; ADACHI, Chihaya; Yasuda, Takuma; Yu Seok, Yang; Kakizoe, Hayato; Mieno, Hiroyuki; US2013/207081; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

52997-43-0, Adding some certain compound to certain chemical reactions, such as: 52997-43-0, name is 7-(Bromomethyl)pentadecane, 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 52997-43-0.

General procedure: General procedure for the synthesis of a1-a6: To a solution of indoline-2,3-diones (10 mmol) in DMF (40 mL) was added K2CO3(15 mmol, 2.073 g) and 7-(bromomethyl)pentadecane (11 mmol,3.358 g) under nitrogen. The mixture was stirred at 70 C and monitoredby TLC. After the reaction completed, water was added, andextracted with EtOAc. The organic layer was combined and dried withMgSO4. After evaporation of the solvent, the residue was purified bycolumn chromatograph (eluent: Petroleum/EtOAc=20:1) to give thetarget compound.

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 52997-43-0.

Reference:
Article; Hu, Qian; Jiang, Hua; Cui, Zhihua; Chen, Weiguo; Dyes and Pigments; vol. 173; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

54879-20-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 54879-20-8 name is 2-Bromo-3-methylaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

EXAMPLE 5 4-(2-Bromo-3-methyl-phenylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester Piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (5.0 g, 21.80 mmol) was dissolved in dry methylene chloride (32 mL) and dry pyridine (4.50 mL). To the reaction mixture was then added thionyl chloride (3.11 g, 26.17 mmol) under nitrogen atmosphere and the reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture was then added successively, under nitrogen atmosphere, 2-bromo-3-methyl-phenylamine (as described in J. Org. Chem. 1998, 53, 1170-1176) (4.46 g, 23.99 mmol), dry triethylamine (7.72 g, 76.33 mmol), dry methylene chloride (40 mL), 4-(dimethylamino)pyridine (0.26 g, 2.18 mmol) and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was then partitioned with aqueous 2N HCl and tert-butyl methyl ether. The organic layer was washed with aqueous 2N HCl, aqueous NaHCO3, brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (30percent ethyl acetate/hexanes) to yield the title compound as a solid. 1H NMR (300 MHz, CDCl3) delta 8.16 (1H, d, J=8.2 Hz), 7.82 (1H, bs), 7.23-7.18 (1H, m), 7.02-6.99 (1H, m), 4.19-4.11 (2H, m), 2.86-2.78 (2H, m), 2.51-2.44 (1H, m), 2.42 (3H, s), 2.04-1.96 (2H, m), 1.78-1.69 (2H, m), 1.47 (9H, s) MS (ES+) m/z 419.0 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-3-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; Battista, Kathleen A.; Bignan, Gilles C.; Connolly, Peter J.; Liu, Jessica J.; Middleton, Steven A.; Orsini, Michael J.; US2007/112016; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

2270-59-9, 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 2270-59-9 as follows.

General procedure: In a well-ventilated fume hood, a 15 mL round-bottomed flaskequipped with a Teflon-coated magnetic stirrer bar was chargedwith NiBr2¡¤3H2O (40.9 mg, 0.150 mmol, 0.05 equiv), bathophenanthroline(4; 49.9 mg, 0.150 mmol, 0.05 equiv), DMF (2.0 mL), andalkyl bromide 2 (3.3 mmol, 1.1 equiv). The vessel was stopperedwith a rubber septum and heated to 40 C in a fume hood until agreen homogeneous solution formed (~20 min). The vessel wasthen removed from the heat and 2-halopyridine 1 (3.00 mmol, 1.00equiv) and manganese(0) (-325 mesh; 330 mg, 6.00 mmol, 2.00equiv) were added. The vessel was resealed with the septum, purgedwith argon, and heated again to 40 C while the progress of the reactionwas monitored by GC analysis of aliquots of the crude reactionmixture. In general, the mixtures turned dark brown or blackwhen the reaction was complete. Upon completion of the reaction,the mixture was cooled to r.t., diluted with Et2O (10 mL), and filteredthrough a short pad of Celite 545 (approx. 1 ¡Á 1 ¡Á 1 inch) wettedwith Et2O (~10 mL) to remove metal salts. The Celite pad waswashed with additional Et2O (2 ¡Á 10 mL), and the filtrate was transferredto a separatory funnel and washed with 1 M aq NH4Cl (10mL). The layers were separated and the aqueous layer was washedwith additional Et2O (3 ¡Á 10 mL). The organic extracts were combined,washed with brine (10 mL), dried (MgSO4), filtered, and concentratedunder reduced pressure. The crude products were purifiedby flash column chromatography on silica gel.

According to the analysis of related databases, 5-Bromo-2-methylpent-2-ene, the application of this compound in the production field has become more and more popular.

Reference:
Article; Everson, Daniel A.; Buonomo, Joseph A.; Weix, Daniel J.; Synlett; vol. 25; 2; (2014); p. 233 – 238;,
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. 876-53-9, name is 1,3-Dibromoadamantane, A new synthetic method of this compound is introduced below., 876-53-9

1. Under nitrogen protection, add 440g of 1,3-dibromoadamantane to a 10L four-necked flask and add 2.0L of Ethyl chloride was stirred well and 500 g of propionic acid aniline was added and stirred well. Add zinc dichloride slowly and stir it well, then heat up to reflux (internal temperature 80-85C). Partially separate the water with a water separator and then use a reflux device. After refluxing at this temperature for 24 hours, the lower layer was a viscous solid and the upper layer was a dichloroethane solvent. Cooled to room temperature, the upper solvent was decanted, 1.0 L DMF was added to warm the solid as a mobile slurry, the slurry was slowly poured into stirred 4.0 L of water, stirred for 30 minutes and filtered to obtain a crude solid wet weight 1015 g, The solid was added to 6L of water for 3.5 hours, filtered and pumped until no liquid was dripped and washed with water (2 x 2L). 1118 g of crude wet weight was obtained, refluxed with 2 volumes of ethanol (3 L) for 1 hour, cooled to room temperature and room The mixture was stirred at room temperature for 1 hour. The wet weight of 439 g was filtered, and used directly for the second-step reaction

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; Shanghai Bodong Chemical Technology Co., Ltd.; Fu Zhiwei; He Baoyuan; Pan Xingang; Yu Wenqing; Li Yongli; Lu Wei; (7 pag.)CN107673977; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

86845-27-4, These common heterocyclic compound, 86845-27-4, name is 5-Bromo-2-methylbenzotrifluoride, 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.

[00478] To a solution of 4-bromo-1-methyl-2-(trifluoromethyl)benzene (6 g, 25.1 mmol), 2-Di-t-butylphosphino-2′,4′,6′-tri-i-propyl-1, -biphenyl (848 mg, 2.0 mmol), Pdidbas (4.6 g, 5.0 mmol) and KOH (4.2 g, 75.3 mmol) in dioxane (40 mL) and water (40 mL) under N2. The mixture was stirred at 100 C for 2.5 h. The reaction was quenched with ice-water, the pH adjusted to 5 with I N HCl aqueous solution, extracted with EtOAc, washed with brine, dried over sodium sulfate, concentrated and purified by chromatography (silica, DCM/petroleum ether=l/2) to afford 4-methyl-3-(trifluoromethyl)phenol (3.5 g, 79 %) as a white solid. ESI-MS (EI+, m/z): No mass

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 86845-27-4.

Reference:
Patent; NAVITOR PHARMACEUTICALS, INC.; MAHONEY, Sarah; MOLZ, Lisa; NARAYAN, Sridhar; SAIAH, Eddine; (516 pag.)WO2018/191146; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

55289-36-6, The chemical industry reduces the impact on the environment during synthesis 55289-36-6, name is 3-Bromo-2-methylaniline, I believe this compound will play a more active role in future production and life.

To anhydrous dichloromethane Compound h (410mg, 2.20mmol), Compound f (409mg, 2.20mmol) and DIPEA(380mL, 2.20mmol) was added at 0C, and the resultant was stirred for 1 hour. Reaction was quenched with addtion ofwater and extraction was performed with dichloromethane. The organic phase was washed with a saturated sodiumchloride solution once. The organic phase was dried over anhydrous magnesium sulfate. After filtration, the filtrate wasconcentrated and subjected to column chromatography to give Compound i (696mg, 2.09mmol) at a yield of 96%.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-2-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hefei Institutes of Physical Sicence, Chinese Academy of Sciences; LIU, Jing; LIU, Qingsong; LIANG, Qianmao; CHEN, Yongfei; CHEN, Cheng; WANG, Aoli; WU, Hong; YU, Kailin; WANG, Wei; HU, Chen; WANG, Wenchao; QI, Shuang; WANG, Beilei; WANG, Li; (78 pag.)EP3412657; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 201138-91-2, name is 4,6-Dibromodibenzo[b,d]furan, molecular formula is C12H6Br2O, 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. 201138-91-2

General procedure: The triolborate, dibromides (0.2 mmol), Pd(PPh3)4 (10 mol %), and K2CO3 (2 equiv) were placed in flask under an atmosphere of nitrogen. DMF (15 mL) was added, and heated at 80 C for 14 h. After cooling to room temperature, 15 mL water was added, extracted with dichloromethane, dried over MgSO4, and then purified by chromatography on silica gel.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 201138-91-2, its application will become more common.

Reference:
Article; Li, Gao-Qiang; Yamamoto, Yasunori; Miyaura, Norio; Tetrahedron; vol. 67; 36; (2011); p. 6804 – 6811;,
Bromide – Wikipedia,
bromide – Wiktionary

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, 3814-30-0

N-benzyloxycarbonyl-3-oxobutazine (702 mg, 3 mmol) was added to 15 mL of DMF, and NaH (180 mg, 4.5 mmo 1) was added under argon at room temperature and stirred at room temperature for 1 h. Bromomethylcyclopentane (0.74 mL, 4.5 mmo 1) and warmed to40 C, the reaction was stopped after 4 h, water was added and extracted with ethyl acetate (60 m). The organic layer was washed with saturated NaCl solution (20 mL x2), dried over anhydrous magnesium sulfate, and column chromatography (E: P = 1: 4, E: P = 1: 2) to give the product 560 mg, yield 59.07%

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, (Bromomethyl)cyclopentane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Zhou Jie; Ji Ming; Yao Haiping; Zhou Qin; (57 pag.)CN107098886; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary