Tag: M.W=200-300

22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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. 22385-77-9

To a solution of 3 (1.5 g, 5.6 mmol) in anhydrous toluene (30 mL), 1-bromo-3,5-di-tert-butylbenzene (1.8 g, 6.7 mmol), was added t-BuONa, (1.2 g 13.4 mmol), and P(t-Bu)3 (1.38 mmol, 2.8 mL of a 10 wtpercent hexane solution) under argon. After stirring under reduced pressure, Pd(dba)2 (0.16 g, 0.28 mmol) was added to the solution. The reaction mixture was stirred at 110 ¡ãC for 16 h under argon. The precipitated solid was removed by filtration, and then the residue was washed with toluene (30 mL). After addition of methanol, precipitation occurred in the solution. The solid residue after filtration was washed with methanol (30 mL), and then was recrystallized from acetone to yield 6b (2.2 g, 86percent) as a pale-yellow powder. 6b: mp: 197 ¡ãC; 1H-NMR (400 MHz, CDCl3): delta = 1.40 (s, 18H, DBC-N-Ph-C(CH3)3), 7.40 (s, 2H, aromatic ring), 7.52 (dd, 2H, J = 14.8, 7.6 Hz, aromatic ring), 7.59 (dd, 3H, J = 8.8, 3.6 Hz, aromatic ring), 7.70 (dd, 2H, J = 15.2, 7.2 Hz, aromatic ring), 7.84 (d, 2H, J = 9.2 Hz, aromatic ring), 8.03 (d, 2H, J = 7.6 Hz, aromatic ring), 9.27 (d, 2H, J = 8.8 Hz, aromatic ring); 13C-NMR (75 MHz, CDCl3): delta = 31.474, 35.16, 112.04, 117.43, 122.04, 122.26, 123.35, 125.40, 126.65, 129.07, 129.11, 130.10, 136.23, 138.02, 152.77; FT-IR (nu cm-1): 3100, 3000, 2850, 1600, 1400, 1350, 1300, 1250, 900, 675; HRMS calcd. for C34H33N ([M+Na]+): 478.2505, found: 478.2506.

Statistics shows that 22385-77-9 is playing an increasingly important role. we look forward to future research findings about 1-Bromo-3,5-di-tert-butylbenzene.

Reference:
Article; Hassan, Fathy; Kawamoto, Masuki; Salikolimi, Krishnachary; Hashizume, Daisuke; Hirose, Takuji; Ito, Yoshihiro; Tetrahedron Letters; vol. 59; 2; (2018); p. 99 – 102;,
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156682-52-9, 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. 156682-52-9, name is 1,4-Dibromo-2,3-difluorobenzene, A new synthetic method of this compound is introduced below.

1,4-Dibromo-2,3-difluorobenzene (15 g, 55.2 mmol), (2-methoxyphenyl) boronic acid in a mixture of water (140 ml) and dioxane (140 ml)(8.80 g, 57.9 mmol), sodium carbonate(11.69 g, 110 mmol) and tetrakis(Triphenylphosphine) palladium (0)(3.19 g, 2.76 mmol) was dissolved.The reaction mixture was degassed and heated in an 80 C. oil bath for 20 hours. The reaction mixture is cooled to room temperature, mixed with brine,Extracted with EtOAc. Washing the extract with water and brine;Dry and evaporate to obtain a solid / liquid mixture,Adsorbed on a silica gel plug,Subjected to silica gel column chromatography,Elution with heptane as a colorless oil4-Bromo-2,3-difluoro-2′-methoxy-1,1′-biphenyl was obtained.(12.5 g, 75% yield).

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; Universal Display Corporation; Zhiqiang, Ji; Jui Yi, Tsai; Alexey, Borisovich Dyatkin; Chun, Lin; (197 pag.)JP2019/127489; (2019); A;,
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393-36-2, Name is 4-Bromo-3-(trifluoromethyl)aniline, 393-36-2, 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.

Starting material laa;4-Bromo-N -ethyl-5-trifluoromethyl-benzene-l,2-diamineStep 1: N-(4-bromo-2-nitro-5-trifluoromethyl-phenyl)-acetamideFollowing the method of Ognyanov, V. L, et. al; /. Med. Chem.; 49(12); 3719(2006), under a nitrogen purge, 4-bromo-3-trifluoromethylaniline (7.2 g; 0.03 mol) was added to acetic anhydride (30 mL) in a 100 mL round-bottomed flask. After stirring for 16 h at room temperature, solvent was removed under reduced pressure to obtain a white solid, which was used as-is for the nitration step.

Statistics shows that 4-Bromo-3-(trifluoromethyl)aniline is playing an increasingly important role. we look forward to future research findings about 393-36-2.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/56150; (2008); A1;,
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Some common heterocyclic compound, 608-30-0, name is 2,6-Dibromoaniline, molecular formula is C6H5Br2N, 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. 608-30-0

EXAMPLE 42; N-[(2-(2,6-Dibromolphenyl)-1-{[4-(1,1-dimethylethyl)phenyl]methyl}-4-hydroxy-6-oxo-1,6-dihydro-5-pyrimidinyl)carbonyl]glycine; 42a) 2,6-Dibromobenzonitrile; 2,6-Dibromoaniline (0.251 g, 1.00 mmol) was added to a stirred solution of copper (I) cyanide (0.116 g, 1.30 mmol) in dimethylsulfoxide (10 mL) at 50 C. under nitrogen. tert-Butyl nitrite (0.357 mL, 3.00 mmol) was injected over 5 min and the mixture stirred for 1 h at 50 C., then cooled and poured into 1 M aqueous hydrochloric acid (100 mL). The mixture was extracted with ethyl acetate and the extracts washed with water, brine, then dried (MgSO4). The solvent was evaporated under reduced pressure and the residue chromatographed (silica gel, 1-9% methanol/dichloromethane) to give the title compound (0.100 g, 38%). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 7.33 (t, J=8.08 Hz, 1 H) 7.67 (d, J=8.08 Hz, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 608-30-0, its application will become more common.

Reference:
Patent; Shaw, Antony N.; Duffy, Kevin J.; Tedesco, Rosanna; Wiggall, Kenneth; US2008/171756; (2008); A1;,
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28342-75-8, 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. 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, A new synthetic method of this compound is introduced below.

1. Add 1 mmol of 1,5-dibromo-2,4-difluorobenzene, 2.2 mmol of nitrogen-containing heterocyclic compound and 2.27 mmol of potassium carbonate to 5 mL of dimethyl sulfoxide.Then reacted for 6 h under an argon atmosphere at a temperature of 130 C.Obtaining a mixed solution I containing a reactant;The mixed solution I containing the reactant was extracted with a mixture of water and dichloromethane, and then the organic layer obtained after the extraction was dried using anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure using a rotary evaporator to give a crude reaction. Product I; using solvent I as a rinse, the crude reaction product I is purified by column chromatography to obtain 1,5-dicarbazole-2,4-dibromobenzene;The nitrogen-containing heterocyclic compound described in the first step is oxazole;The solvent I described in the first step is a mixed solution of petroleum ether and dichloromethane, the volume ratio of petroleum ether to dichloromethane in the solvent I is 5:1;The volume ratio of water to dichloromethane in the mixture of water and dichloromethane described in the first step is 1:5;

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; Heilongjiang University; Xu Hui; Duan Chunbo; Han Chunmiao; Liang Qianqian; (46 pag.)CN107325811; (2019); B;,
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Adding a certain compound to certain chemical reactions, such as: 61613-22-7, name is 2-Bromo-N-phenylaniline, 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 61613-22-7, 61613-22-7

After dissolving 10 g of 2-bromo-N-phenylphenylamine in 100 ml of tetrahydrofuran,The reaction temperature was lowered to -78 C, 20 ml of 2.5 M butyllithium was slowly added dropwise and stirred for 1 h.15.2 g of bis (4-chlorophenyl) methanone was dissolved in 150 ml of tetrahydrofuranAfter slowly adding dropwise, the temperature was increased to room temperature and stirred for 12 h. After the reaction is completed, distilled water and water will be usedMethylene chloride and dried under anhydrous magnesium sulfate and then filtered under reduced pressure, without further purificationPure and directly dissolved in 150 ml of acetic acid, 10 ml of sulfuric acid was added dropwise and the mixture was stirred under reflux. After the reaction is over, useDistilled water and methylene chloride and the resulting solid was subjected to column purification to give compound 9-1 (10 g, yield62%).

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, 2-Bromo-N-phenylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Liu Xiqing; Cai Hui; (24 pag.)CN107400085; (2017); A;,
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626-40-4, A common heterocyclic compound, 626-40-4, name is 3,5-Dibromoaniline, molecular formula is C6H5Br2N, 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.

Compound II (2.25 g, 10 mmol), compound III (2.51 g, 10 mmol) and diisopropylethylamine (DIPEA,3.88 g, 30 mmol) was dissolved in 50 mL of dry xylene and then warmed under nitrogen protection until the reaction was complete (usually 5 hours). The reaction mixture was carefully poured into 200 mL of ice water, stirred, extracted with 50 mL of X3CH2C12, the combined extracts were washed successively with 1% dilute hydrochloric acid (200 mL) and brine (100 mL) and dried over anhydrous sodium sulfate. The filtrate was evaporated to dryness on a rotary evaporator to give compound IV, white solid.

The synthetic route of 3,5-Dibromoaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Sai Bo Technology Co., Ltd.; Guo Huijun; (11 pag.)CN106749370; (2017); A;,
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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;,
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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. 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,
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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