Category: bromides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 1647-26-3, name is 1-Bromo-2-cyclohexylethane, 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 1647-26-3, Safety of 1-Bromo-2-cyclohexylethane

To a solution of chloro-6-methyl-2-[2-(methyloxy)phenyl]-4(1 H)-pyrimidinone (0.42g, 1.7 mmoles) in DMF were added lithium hydride (0.027g, 3.4 mmoles), lithium bromide (0.436g, 5.0 mmoles), and 2-cyclohexylethyi bromide (1.6g, 8.4 mmoles). Upon stirring overnight at room temperature, the reaction was quenched with saturated ammonium chloride, extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, concentrated in vacuo and the residue purified by flash chromatography (0-30% ethyl acetate/hexane) to afford the desired product (0.23g, 38%). Subsequent deprotection using BBr3 was accomplished to produce the title compound (0.2g, 90%). MS (m/z): 347.2 [M+ H]+.

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:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/62370; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 167355-41-1,Some common heterocyclic compound, 167355-41-1, name is 6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine, molecular formula is C10H12BrN, 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.

Di-tert-butyl dicarbonate (1.030 g, 4.719 mmol) was added to a stirred RT solution of 6-bromo-1,2,3,4-tetrahydro-naphthalen-2-ylamine (0.970 g, 4.290 mmol) in CH2Cl2 (100 mL). TEA (0.897 mL, 6.435 mmol) was added to the reaction and the mixture was stirred at RT until HPLC analysis showed complete consumption of starting material. The reaction was diluted with CH2Cl2, washed with saturated aqueous NaHCO3, dried over MgSO4 and concentrated in vacuo to afford the crude material. The crude was purified by flash column chromatography to yield the title compound. MS (APCI pos) 269 (M-t-Bu).

The synthetic route of 167355-41-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; Array Biopharma, Inc.; US2005/234044; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 4549-33-1, name is 1,9-Dibromononane, molecular formula is C9H18Br2, 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. HPLC of Formula: C9H18Br2

2,2,12,12-Tetramethyltridecanedioic acid diethyl ester (153). Under N2 atmosphere and at -78 C., a solution of lithium diisopropylamide (2 M in heptane/THF/ethylbenzene, 52.5 mL, 105 mmol) was added dropwise to a solution of ethyl isobutyrate (17.4 g, 150 mmol) in THF (50 mL). The mixture was stirred for 1 h and 1,9-dibromononane (151, 14.3 g, 50 mmol) was added, followed by DMPU (4.4 g, 34.3 mmol). The mixture was stirred for 30 min and the cooling bath was removed. After 30 min, the THF was evaporated under reduced pressure. The residue was diluted with saturated NH4Cl solution (300 mL) and extracted with ethyl acetate (3*100 mL). The combined organic layers was washed with brine (200 mL), 5% aqueous HCl (100 mL) and saturated NaHCO3 solution (50 mL), and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was distilled in high vacuo to give 153 (14.0 g, 79%) as an oil. Bp 150-151 C./0.1 mmHg. 1H NMR (CDCl3): delta (ppm): 4.08 (q, J=7.2, 4H), 1.48-0.98 (m, 18H), 1.21 (t, J=7.2, 6H), 1.12 (s, 12H). 13C NMR (CDCl3): delta (ppm): 178.1, 60.0, 42.1, 40.7, 30.0, 29.4, 25.1, 24.8, 14.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4549-33-1, its application will become more common.

Reference:
Patent; Dasseux, Jean-Louis Henri; Oniciu, Carmen Daniela; US2004/192771; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 327-52-6, A common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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.

4.2 mL of 1-bromo-2,4,5-trifluorobenzene and 10.8 mL of tetrahydrofuran were added to 50 mL flask and the resulting reaction solution was cooled to 0 C. 15 mL of isopropylmagnesium chloride [2.0 M tetrahydrofuran solution] was dropped to the reaction solution under nitrogen atmosphere and stirred for 30 minutes to produce Grinard reagent. 1.95 g of (S)-t-butyl 2-(2-t-butoxy-2-oxoethyl)aziridine-1-carboxylate and 50 mL of tetrahydrofuran were added to another 250 mL flask and the resulting reaction solution was cooled to 0 C. And then, 778 mg of copper (I) bromide dimethylsulfide complex was added. 22.7 mL of the Grinard reagent produced under nitrogen atmosphere was dropped, and stirred for 6 hours while the reaction temperature was maintained at 0 C. After completing the reaction, 50 mL of ammonium chloride aqueous solution was dropped to the reaction solution; 100 mL of ethyl acetate and 50 mL of water were added and then stirred for 10 minutes. An organic layer was isolated, dehydrated with magnesium sulfate, and then concentrated under reduced pressure. A concentrated residue was isolated with column chromatography (n-hexane:ethyl acetate=20:1) and then concentrated under reduced pressure to obtain 2.62 g of a title compound. 1H NMR (CDCl3, 400 MHz) delta 7.02 (m, 1H), 6.87 (m, 1H), 5.11 (br, 1H), 4.07 (br, 1H), 2.82 (dd, 1H), 2.77 (dd, 1H), 2.45 (dd, 1H), 2.35 (dd, 1H), 1.44 (s, 9H), 1.35 (s, 9H)

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DONG-A PHARMACEUTICAL. CO., LTD; US2012/16126; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 5433-01-2, 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. 5433-01-2, name is 1-Bromo-3-isopropylbenzene, This compound has unique chemical properties. The synthetic route is as follows.

Method 72; 3-Isopropylbenzoic acid; A solution of l-bromo-3-isopropylbenzene (500 mg, 2.51 mmol) in pentane/ether (1:1; 8 ml) was treated with t-butyllithium (1.7 M in pentane, 3.0 ml) at -78 C. The mixture was stirred at -78 0C for 10 min and then CO2 (g) was bubbled into the mixture for several minutes. The reaction was quenched with 10% HCl and extracted with EtOAc. The organic layer was dried with NaCl (sat) then Na2SO4 (s). The solvents were removed under reduced pressure to give a white solid (379 mg, 92%); m/z 166.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/40568; (2006); A1;,
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. 7745-91-7, name is 3-Bromo-4-methylaniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H8BrN

3-Bromo-4-methylaniline (30.4 g) was dissolved in methanol (210 mL), pyridine (43 mL) and iodine (68.4 g) were added, and the mixture was stirred at 25C for two hours. A 20% aqueous sodium thiosulfate solution (150 mL) and water (30 mL) were added to the reaction solution and the mixture was stirred at 25C for one hour. Washing with methanol/water (1/1, 100 mL) resulted in the target compound (19.1 g).

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; Chugai Seiyaku Kabushiki Kaisha; F. Hoffmann-La Roche AG; EBIIKE, Hirosato; AOKI, Toshihiro; CHIBA, Takashi; KOCHI, Masami; NAKAMA, Kimitaka; NIIZUMA, Satoshi; NISHII, Hiroki; OHWADA, Jun; SHIMAMURA, Hiroyuki; SUGE, Aiko; NAKANISHI, Yoshito; KOBAYASHI, Natsuki; (594 pag.)EP3312172; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 4885-18-1, name is 1-(3-Bromophenyl)-N,N-dimethylmethanamine, molecular formula is C9H12BrN, 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. Computed Properties of C9H12BrN

Dimethylamine 49 (1.31 g, 6.13 mmol) was dissolved in anhydrous THF (15 ml) under Ar(g) in a flame-dried round-bottomed flask equipped with a reflux condenser. To facilitate generation of the Grignard reagent, a catalytic amount of 12 was added to the solution. Crushed magnesium turnings (223 mg, 9.2 mmol) were then added to this solution, and the resulting solution was heated at reflux for 2 hr to generate the Grignard reagent. In a separate flamed-dried flask, diethyl phosphite (237 mul, 1.84 mmol) was dissolved in anhydrous THF (1.0 ml), and cooled to 0 C. with an ice bath. The solution of Grignard reagent was added dropwise to this solution, and the resulting solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was then quenched with water (1 ml), and the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2, and the resulting solution was washed with water and brine. The combined organic extracts were dried over anhydrous MgSO4(s) and filtered, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica gel, 20% v/v MeOH in CH2Cl2) to give phosphine oxide 50 as a colorless oil in 66% yield. 1H NMR (CDCl3, 400 MHz) delta 8.06 (d, J=1.2 Hz, 1H), 7.69 (s, 1H), 7.66 (s, 1H), 7.58 (t, J=7.5 Hz, 2H), 7.54 (dd, J=8.9, 1.2 Hz 2H), 7.45 (dd, J=7.6, 3.1 Hz 2H), 3.45 (s, 4H), 2.22 (s, 12H) ppm; 13C NMR (CDCl3, 100.6 MHz) delta 140.22 (d, J=10.7 Hz), 133.45, 132.15, 131.31 (d, J=12.2 Hz), 129.67 (d, J=11.2 Hz), 129.14 (d, J=12.2 Hz), 64.06, 45.58 ppm; 31P NMR (CDCl3, 161 MHz) delta 22.02 ppm; MS (ESI) m/z 288.0393 (MH+[C18H25N2OPH+]=288.0383).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4885-18-1, its application will become more common.

Reference:
Patent; Wisconsin Alumni Research Foundation; Raines, Ronald T.; Tam, Annie; Soellner, Matthew B.; US8410247; (2013); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 858121-94-5, name is 4-(Bromomethyl)-1,1-difluorocyclohexane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-(Bromomethyl)-1,1-difluorocyclohexane

General procedure: DIPEA (778 muIota, 4.46 mmol) was added dropwise to a stirred solution of N-(2-hydroxyethyl)-4- (2H-tetrazol-5-yl)benzenesulfonamide (300 mg, 1.1 14 mmol, Intermediate 17′) and 2- (bromomethyl)tetrahydro-2H-pyran (285 muIota, 2.228 mmol, commercial source: Aldrich) in N,N- Dimethylformamide (DMF) (3714 muIota) at rt under nitrogen. The mixture was stirred at rt for 3 days. As starting material remained, it was stirred at 70 C overnight. The mixture was concentrated under reduced pressure. The crude compound was purified by flash column chromatography (silica; EtOAc-cyclohexane from 0/100 to 50/50). The desired fractions were collected and concentrated in vacuo to obtain the product as a racemic mixture N-(2- hydroxyethyl)-4-(2-((tetrahydro-2H-pyran-2-yl)methyl)-2H-tetrazol-5-yl)benzenesulfonamide (49 mg, 0.133 mmol, 28%). NMR (400 MHz, Acetone-d6) delta 7.84-7.78 (m, 2H), 7.56-7.50 (m, 2H), 7.33 (t, J = 5.9 Hz, 1 H), 4.37-4.32 (m, 2H), 4.25 (t, J = 5.6 Hz, 1 H), 3.50-3.44 (m, 1 H), 3.38-3.32 (m, 1 H), 2.94-2.90 (m, 2H), 2.86-2.80 (m, 1 H), 2.41-2.37 (m, 2H), 1.40-1.25 (m, 2H), 1.12-0.85 (m, 4H). MS m/z [M-H]”= 366.2

According to the analysis of related databases, 858121-94-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ALEMPARTE-GALLARDO, Carlos; ENCINAS, Lourdes; ESQUIVIAS PROVENCIO, Jorge; (206 pag.)WO2019/34729; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 3972-64-3, 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. 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1-bromo-3-(tertbutyl)benzene (300 mg, 1.41 mmol) was dissolved in dry THF (5 mL) at -78 C under nitrogen and was stirred for 10 min. n-BuLi (2.5 M in hexanes, 2.0 mL, 4.9 mmol) was added drop wiseto the solution was stirred for 2 h at -78 C. After two hours, ethyl fluoroacetate (0.16 mL, 1.69mmol) was added drop wise and stirred for 1 min at -78 C upon which the mixture was then quenched with NH4Cl (20 mL) and warmed to room temp. The mixture was then extracted withether (50 mL), and dried over MgSO4. After concentration in vacuo (note: remove shortly afterthe ether is removed, because the compound is quite volatile), the residue was purified with flash chromatography over silica gel (hexane: ethyl acetate = 90:10) to yield the product as a yellowliquid in 43percent yield (0.12 g).

The synthetic route of 1-Bromo-3-(tert-butyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Camerino, Eugene; Wong, Dawn M.; Tong, Fan; Koerber, Florian; Gross, Aaron D.; Islam, Rafique; Viayna, Elisabet; Mutunga, James M.; Li, Jianyong; Totrov, Maxim M.; Bloomquist, Jeffrey R.; Carlier, Paul R.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4405 – 4411;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 58971-11-2, name is 3-Bromophenethylamine, 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 58971-11-2, Quality Control of 3-Bromophenethylamine

General procedure: Toa solution of 2a (20.0 g, 0.1 mol)and triethylamine (30.3 g, 0.3 mol) in DCM (350 mL) was added ethylchloroformate (12.9 g, 0.1 mol) dropwise at 0 oC and then stirred atroom temperature for 3 h. The reaction mixture was washed with 3M HCl (100 mL×2), dried over Na2SO4 and concentrated under reducedpressure. The residue was purified by silica gel column chromatography (PET/EA= 25:1, v/v) to afford compound 3a as colorless oil (22.3 g, 82.0%).

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

Reference:
Article; Sun, Zhaozhu; Zhou, Tian; Pan, Xuan; Yang, Ying; Huan, Yi; Xiao, Zhiyan; Shen, Zhufang; Liu, Zhanzhu; Bioorganic and Medicinal Chemistry Letters; vol. 28; 18; (2018); p. 3050 – 3056;,
Bromide – Wikipedia,
bromide – Wiktionary