Tag: M.W=200-300

A common compound: 51554-93-9, name is 1-Bromo-4-octylbenzene, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 51554-93-9

To synthesize intermediate compound 16d, n-BuLi (2.5 M in hexane, 146 muIota_, 0.364 mmol) is added dropwise to a solution of 1 -bromo-4-octylbenzene (16a) (94 mg, 0.350 mmol) in THF (0.53 ml_) at -78 C. After stirring for 0.5 h, 16c (40 mg, 0.14 mmol) in THF (0.1 ml_) is added to the mixture, and the solution is stirred for an additional 2 h at-78 C. The reaction is then warmed to -40 C and stirred overnight. The reaction mixture is quenched at -40 C with saturated NH4CI solution and allowed to warm to room temperature. The organic layer is separated and the aqueous layer is extracted three times with CH2CI2. The combined organic layers are washed with brine, dried over MgS04 and filtered. The solvent is removed under reduced pressure and the residue is purified by flash chromatography (hexane: EtOAc, 12: 1 to 8: 1 ) to give compound 16d (21 mg, 32 %) as a slightly yellow 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, 51554-93-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; THE UNIVERSITE DE MONTREAL; EDINGER, Aimee; HANESSIAN, Stephen; (172 pag.)WO2017/53990; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, molecular formula is C6H3Br2F, 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. 1435-51-4

To mixture of l,3-dibromo-5-fluorobenzene (LXX) (100 g, 393 mmol) and N’,N’-dimethylethane-l,2-diamine (173 g, 1.97 mol, 214 mL) was added t-BuOK (88 g, 787 mmol) in one portion at 25C under N2. The mixture was stirred at 25C for 30 min, then heated to 1 10C and stirred for 1 1.5 h. The mixture was cooled to 25C and concentrated in reduced pressure at 45C. The residue was purified by silica gel chromatography (column height: 250 mm, diameter: 100 mm, 100-200 mesh silica gel, PE/EtOAc = 2: 1, Rf = 0.6) to give N:-(3- bromo-5-fluorophenyl)-N2,N2-dimethylethane-l,2-diamine (LXXI) (30 g, 1 14.9 mmol, 29.2% yield) as a yellow oil. ESIMS found for Ci0Hi4BrFN2 mlz 261.1 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1435-51-4, its application will become more common.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (251 pag.)WO2017/24003; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 73918-56-6 name is 2-(4-Bromophenyl)ethanamine, 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. 73918-56-6

General procedure: To a solution of neocrotocembraneic acid (150 mg, 0.50 mmol) in dry CH2Cl2 (10 mL) were added HOBt (81 mg, 0.60 mmol) and EDCI (115 mg, 0.60 mmol). The mixture was stirred at room temperature for 2 h, and then the corresponding amines (0.6 mmol 1.2 equiv.) were added. Upon completion, the reaction mixture was washed successively with 1M hydrochloric acid, saturated NaHCO3 and brine, then dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography to give the amide derivatives 8a-8r.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Bromophenyl)ethanamine, and friends who are interested can also refer to it.

Reference:
Article; Shang, Hai; Li, Ling-Yu; Cheng, Wei-Hua; Luo, Jun; Zhang, Hong-Wu; Zou, Zhong-Mei; Molecules; vol. 21; 11; (2016);,
Bromide – Wikipedia,
bromide – Wiktionary

1435-51-4, 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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To 2,6-dimethoxyphenylboronic acid (4.50 mmol, 819 mg) in a mixture of toluene (45.0 mL), 2 M aqueous Na2CO3 (18.0 mL) and EtOH (9 mL) were successively added under Argon 1-fluoro-3-iodo-benzene (3.00 mmol, 666 mg) and Pd(PPh3)4 (0.15 mmol, 173 mg). This well-stirred mixture was heated at reflux for 18 h and then diluted at 25 C with water (100 mL) and toluene (50 mL). The aqueous layer was separated and washed with CH2Cl2 (2 ¡Á 100 mL). All the organics layers were combined, dried over Na2SO4 and concentrated under reduced pressure. Purification of the residue by column chromatography (cyclohexane/CH2Cl2 75:25) followed by crystallization from MeOH afforded biaryl 4a as a colorless solid (380 mg, 55%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Diemer, Vincent; Garcia, Juan Sanz; Leroux, Frederic R.; Colobert, Francoise; Journal of Fluorine Chemistry; vol. 134; (2012); p. 146 – 155;,
Bromide – Wikipedia,
bromide – Wiktionary

69272-50-0, name is 3,6-Dibromobenzene-1,2-diamine, 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. 69272-50-0

Dissolve 3,6-dibromobenzene-1,2-diamine (10g, 37mmol) and 1,2-diphenyl-1,2-ethanedione (7.9g, 37mmol) in ethanol (250ml, 0.15M) in a two-neck round bottom flask And refluxed under nitrogen at 100 C. for one day.The temperature was lowered to room temperature and filtered to obtain Compound 2-A (light yellow solid). (Yield 16g, Yield 96%)

Statistics shows that 69272-50-0 is playing an increasingly important role. we look forward to future research findings about 3,6-Dibromobenzene-1,2-diamine.

Reference:
Patent; LG Chem, Ltd.; Lee Ji-yeong; Kim Sang-a; Ryu Seung-jun; Kim Ji-hun; (26 pag.)KR2019/86210; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

3638-73-1, These common heterocyclic compound, 3638-73-1, name is 2,5-Dibromoaniline, 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.

2,5- dibromo aniline (compound 1, 7.53 g, 30 mmol), Chloral monohydrate (5.95 g, 36 mmol), hydroxy amine – hydrogen chloride (3.13 g, 45 mmol) and sodium sulfate (30.0 g) were added into a mixed solvent of water (100 mL) & ethanol (100 mL). These mixture was heated-refluxed for 12 hours at 80C. Thereafter, ethanol was removed under reduced pressure, concentrated, and when poured into crushed ice, a white solid was precipitated. As it is, allowed to stand for 3 hours at 0C, then the precipitated white solid was recovered by filtration, and dried in air to obtain 8.28 g (86%) of 2,5- dibromo isonitroso acetoanilide (compound 2). Subsequently, this compound 2 was heated for 15 mins at 100C in 86% sulfuric aicd (80 mL), to proceed the cyclization reaction, and the color of the reaction product changes to dark red. Here the resulting product was poured into crushed ice and 4.96 g (63%) of 3,6- dibromo isatin (compound 3) was precipitated as light orange crystals. Then, the produced compound 3 was done hydrolysis under basic conditions by adding hydrogen peroxide and 3.79 g (79%) of 3,6- dibromo Anthranilic Acid (compound 4) was obtained as Dull white crystals. Finally, compound 4 was done diazotization under the existence of nonproton, and by doing this, it is possible to change to 1,4- dibromo- 2,3- diiodo benzene (compound 5). Hexane as eluent, by silica gel column chromatography or by distillation under reduced pressure, compound 5 was obtained as white crystals with yield 35% (2.19 g).

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 3638-73-1.

Reference:
Patent; ADEKA Corporation; Nishihara, Yasushi; Chang, Ning Huei; Iwasaki, Masayuki; (22 pag.)JP6132656; (2017); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, 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 73918-56-6. 73918-56-6

To a solution of 2- (4-bromophenyl) ethylamine (27 g, 0.13 mol) andTriethylamine (16.4 g, 0.16 mol) in anhydrous dichloromethane (300 ml) was added dropwise a solution of trifluoroacetic anhydride(34 g, 0.16 mol). The reaction mixture was stirred at room temperature for 1 hour and then diluted with water.The organic layer was separated and concentrated to dryness under vacuum to give N- (4-bromophenethyl) -trifluoroacetamide(37 g, 96.1%) as a white solid.

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 2-(4-Bromophenyl)ethanamine.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; DING, ZHAO ZHONG; WU, HAO; SUN, FEI; WU, LI FANG; YANG, LING; (97 pag.)TWI558709; (2016); B;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 24358-62-1 name is 1-(4-Bromophenyl)ethylamine, 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. 24358-62-1

Library Protocol I To a 0.2M solution of 5-(4,4, 5,5-tetramethyl- 1, 3,2-dioxaborolan-2-yl)-2-[( 1 -{[4-(trifluoromethoxy) phenyl]acetyl}piperidin-4-yl)oxy]pyridine-3-carboxamide (Preparation 13, 500 pL, 100 pmol) in DMF was added a 0.2M solution of compounds of formula (IV) (500 pL, lOOpmol) in DMF with argon purging. A 2M solution of cesium carbonate (100 pL, 200 pmol) in degassed water was added followed by tetrakis(triphenylphosphine)palladium (0) (5.7 mg, 5 pmol) and the reaction was heated to 11000 under microwave irradiation for 15 minutes. Thereaction was cooled and concentrated in vacuo. the residue was dissolved in DMSO (1 mL) and purified using preparative HPLC using one of the Purification Methods (PM) below:

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Bromophenyl)ethylamine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

The chemical industry reduces the impact on the environment during synthesis 7766-50-9, name is 11-Bromo-1-undecene, I believe this compound will play a more active role in future production and life. 7766-50-9

p-Benzenediol (Hydroquinone, defined as BP1 here) (2.2 g,20 mmol) and sodium hydroxide (2.4 g, 60 mmol) were dissolved in 120 mL DMF in a 250-mL round bottomed Schlenk flask, then themixture was stirred for 30 min, and a solution of 11-bromo-1-undecene (12 g, 51.5 mmol) in DMF (120 mL) was added dropwise over 10 min. The resulting reaction mixture was heated at 70 C and left stirring for more than 8 h. Subsequently, the reaction was cooled to RT and quenched with addition of diethyl ether (100 mL) and water (100 mL). The aqueous phase was extracted with diethyl ether (300 mL 2), and the combined organic fractions were washed with brine and dried over MgSO4 and concentrated. The residue was recrystallized from EtOH twice to obtain 6.1 g BP1-M1. Yield: 74%.

The chemical industry reduces the impact on the environment during synthesis 7766-50-9. I believe this compound will play a more active role in future production and life.

Reference:
Article; Song, Shaofei; Miao, Weijun; Wang, Zongbao; Gong, Dirong; Chen, Zhong-Ren; Polymer; vol. 64; (2015); p. 76 – 83;,
Bromide – Wikipedia,
bromide – Wiktionary

28342-75-8, Adding a certain compound to certain chemical reactions, such as: 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, 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 28342-75-8.

To a solution of 1,5-dibromo-2, 4-difluorobenzene (Nucleosides, Nucleotides nucleic Acid, 201 (1 and2), 11-40 (2001) ) (8.8 g, 32.4 mmol) in diethylether (60 ml), 1.6 M n-BuLi in hexane (24.3 ml, 1.2 eq) was added at-78 C under N2 atmosphere. After stirring the reaction mixture at-78 C for 30 min, N-methyl-N- (methyloxy) acetamide (5.0 g, 1.5 eq) was dropped into to quench the reaction. The reaction mixture was stirred at the same temperature for further 30 min. After added acetic acid ( (5.2 ml), water (78 ml), the reaction mixture was extracted with diethylether. The obtained organic phase was washed by 0.2 N HCI aqueous, water, saturated NaHC03 aqueous and saturated NaCI aqueous, and dried over MgS04. After removing the solvent under reduced pressure, the residue was purified by Silica gel chromatography (n-Hexane/EtOAc = 49/1). Desired compound was obtained as pale yellow oil (4.94 g, 65percent).

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, 1,5-Dibromo-2,4-difluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/85227; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary