Author: Jessica.F

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. 656-64-4, name is 3-Bromo-4-fluoroaniline, A new synthetic method of this compound is introduced below., Product Details of 656-64-4

Compound 50d (0.6 g, 2.3 mmol),3-bromo-4-fluoroaniline (0.47 g, 2.5 mmol),HATU (0.95g, 2.5mmol)And triethylamine (0.35 g, 3.5 mmol) was dissolved in N,N-dimethylformamide (15 mL).Stir at room temperature for 3 hours.Ethyl acetate was added, and the organic phase was washed four times with water, washed twice with brine, dried over anhydrous sodium sulfateTo give crude title compound 50e (0.88g, 2.0mmol) purified by column chromatography, a yield of 87%.

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 Huahuituo Pharmaceutical Technology Co., Ltd.; Zhejiang Huahai Pharmaceutical Co., Ltd.; Xu Xin; Zhang Tian; Li Yunfei; Wang Guan; Zhu Weibo; Li Dongsheng; Qin Chenggang; Liu Chuanduo; Liu Lei; Wu Qimei; Yang Xuqin; Jia Jie; Wang Ying; Chen Yuhao; Wang Yijin; Ge Jian; (143 pag.)CN109897011; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2635-13-4, A common heterocyclic compound, 2635-13-4, name is 5-Bromobenzo[d][1,3]dioxole, molecular formula is C7H5BrO2, 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.

EXAMPLE 3 Alternative Syntheses of (s)-alpha-methyl-1,3 benzodioxole-5-ethanol 3.47 grams of 4-bromo-1,2(methylenedioxy)benzene were dissolved in 100 ml of tetrahydrofuran at -78 C., 13.9 ml of 1,3M sec-butyllithium in cyclohexane was then added to consume the aryl halide in less than 30 minutes. 1.00 grams of (S)-(-)-propylene oxide in 2 ml THF was added by syringe and the solution stirred for 45 minutes. The solution was then warmed to 23 C. for 16 hours. The reaction mixture wag poured into 3M ammonium chloride solution and the product isolated by extraction with ethyl acetate. The combined extracts were dried over magnesium sulfate filtered through florisil and concentrated by rotary evaporation. The residual oil was purified by silica gel chromatography and eluted with a 50:50 mixture of hexane and diethyl ether to yield 1.40 g (45%) of the subtitled intermediate. Pchem: [alpha]365+117.2 (c 1.0, CHCl3) TLC Rf=0.26 (50:50 hexane:ether); IR (CHCl3) 3598, 3012, 2973, 2887, 1490, 1249, 1041 cm-1; 13C NMR (CDCl3) d 147.75, 146.19, 132.26, 122.27, 109.68, 108.30; mass spectrum, m/z (FD, M+) 180; Anal. Calcd. for C10H12O3: C, 66.65; H, 6.71. Found: C, 66.42; H, 6.66.

The synthetic route of 2635-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US6329364; (2001); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 111721-75-6, name is 2-Bromo-3-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: bromides-buliding-blocks

This Example made use of the general preparative method designated Route C. 3-Methyl4-nitrobenzoyl chloride (0.2 mol) was added slowly to a solution of 2-bromo-3-fluoroaiiiline (0.2 mol) in pyridine (100 ml). The resulting solution was heated under reflux for 60 min, then poured into water (300 ml). The precipitate was filtered from solution, washed with water (100 ml), followed by methanol to afford a white solid. [00126] Lawesson’s reagent (0.07 mol) was added to a solution of the benzanilide obtained (0.1 mol) in HMPA (50 ml). The resulting solution was heated at 100 C. for 15 hr, then poured into water (300 ml). The product was extracted into diethyl ether (3×300 ml) and washed with water (3×200 ml). Evaporation of the solvent followed by recrystallization from methanol gave a bright orange solid. [00127] Sodium hydride (0.22 mol) was slowly added to a solution of the fluoro substituted thiobenzanilide thus obtained (0.2 mol) in N-methyl-2-pyrrolidinone (2 mol) at room temperature with stirring. The mixture was heated at 150 C. for one hour then allowed to cool. Water (50 ml) was then added and the precipitate collected by filtration and dried in vacuo to give the product as a white solid. [00128] The product of the previous step (0.03 mol) and tin(II) chloride dihydrate (0.15 mol) were suspended in ethanol (150 ml) and heated under reflux for 2 hours. The solvent was removed under vacuum and the resulting oil taken up in ethyl acetate (700 ml). The organic layer was washed with 2 M sodium hydroxide. (2×200 ml), water (100 ml) and salt brine (30 ml). Removal of the solvent under vacuum followed by recrystallization from methanol gave the title compound as a pale yellow solid. [00129] mp 175-177 C.; IR 3021, 1621 (CN), 1470, 1215, 750 cm-1.

The synthetic route of 111721-75-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Malcolm, F. G. Stevens; US6858633; (2005); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 3344-70-5, The chemical industry reduces the impact on the environment during synthesis 3344-70-5, name is 1,12-Dibromododecane, I believe this compound will play a more active role in future production and life.

General procedure: A suspension of lithium acetylide ethylenediamine complex (247 mg, 2.70 mmol) in dry DMSO (4 mL) was stirred for 10 min at room temperature under nitrogen. After the mixture was cooled to 8 °C, 1-bromo-7-hexadecyne (708 mg, 2.35 mmol) was added dropwise. The reaction mixture was stirred at rt overnight and cooled to 0 °C. Water (1 mL) was added very slowly. The suspension was stirred for 10 min at rt, then poured into water (60 mL), and extracted with hexane. The combined organic phases were dried (Na2SO4), filtered, evaporated to dryness under reduced pressure, and purified by chromatography (elution with hexane) to give Yield 66percent: 1H NMR delta 1.25 (12H, m, (CH2)6); 1.36 (4H, m, CH2C-C-C?C); 1.49 (4H, m, CH2C-C?C); 1.91 (1H, t, J = 2.6 Hz, C?CH); 2.16 (4H, td, J = 2.6 Hz, J = 7.2 Hz, CH2-C?C); 13C NMR delta 18.4 (C-3 and 14), 28.5 (C-4 and 13), 28.7 (C-5 and 12), 29.1 (C-6 and 11), 29.5 and 29.6 (C-8, 9, 10 and 11), 68.0 (C-1 and 16), 84.8 (C-2 and 15).

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, 1,12-Dibromododecane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Vilchze, Catherine; Leung, Lawrence W.; Bittman, Robert; Jacobs, William R.; Chemistry and Physics of Lipids; vol. 194; (2016); p. 125 – 138;,
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. 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3BrF2

Step 2 4-(2,3-Difluoro-phenyl)-1H-indole 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole 6b (1.22 g, 5 mmol) was dissolved in 20 ml of tetrahydrofuran under stirring, and added with 1-bromo-2,3-difluoro-benzene (0.97 g, 5 mmol), tetrakis (triphenylphosphine)palladium (0.17 g, 0.15 mmol) and sodium hydroxide solution (7 ml, 2 mol/L) under an argon atmosphere. Upon completion of the addition, the reaction system was stirred at 75° C. in an oil bath overnight. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature and extracted with ethyl acetate (20 ml*3). The combined organic extracts were washed with saturated brine (10 ml), dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-(2,3-difluoro-phenyl)-1H-indole 6c (800 mg, yield 70percent) as a white solid. MS m/z (ESI): 228.4 [M-1]

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 38573-88-5.

Reference:
Patent; ChoTang, Peng Cho; Su, Yidong; Li, Yali; Zhang, Lei; Zhao, Fuqiang; Yang, Jialiang; Zhou, Ying; Bie, Pingyan; Qian, Guangtao; Ju, Minggang; US2010/75952; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 2695-48-9,Some common heterocyclic compound, 2695-48-9, name is 8-Bromo-1-octene, molecular formula is C8H15Br, 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.

To a solution of cuprous chloride (0.33 mmol) in Et2O (7 mL) at -78 C. was added a 2.0M solution BnMgBr in THF (13.1 mmol) followed by an alkyl bromide (6.52 mmol) and let warm to r.t. After reacting at r.t. for 20 hours, the reaction was cooled to 0 C. and quenched with 1 n HCl. The mixture was then extracted into three 200 mL portions ethyl acetate, dried with Na2SO4, and concentrated to a black oil. The title product was recovered after purification by flash chromatography. General procedure L was used to convert 5.98 mmol of 8-bromo-1-octene to 5.08 mmol (85%) of the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Bromo-1-octene, its application will become more common.

Reference:
Patent; University of Virginia Patent Foundation; US2012/214858; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 327-52-6 as follows. Application In Synthesis of 1-Bromo-2,4,5-trifluorobenzene

Synthesis P 2′,4′,5′-Trifluoro-/V-((1 s,4s)-4-hydroxy-4-methylcyclohexyl)- [1 , 1 ‘-biphenyl]-4-sulfonamide (HMC-C-10-B) A stirred solution of N-((1 s,4s)-4-hydroxy-4-methylcyclohexyl)-4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)benzenesulfonamide (1.8 g, 4.55 mmol), 1-bromo-2,4,5- trifluorobenzene (2.4 g, 1 1 .4 mmol) and sodium carbonate (1 .2 g, 1 1 .3 mmol) in dioxane: water (30:3 mL) was degassed using argon for 10 minutes. [1 , 1 -Bis(diphenylphosphino) ferrocene] dichloropalladium(ll) (0.333 g, 0.455 mmol) was added and the reaction mixture was degassed for another 10 minutes and stirred at 1 10C for 6 hours. Solvent was evaporated under reduced pressure and the compound was extracted into ethyl acetate. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 230-400 mesh silica gel with 10-60 % ethyl acetate in hexane as eluent. The resulting residue was washed with hexane followed by n-pentane to afford the title compound (0.60 g, 33%). 1H NMR (400 MHz, CDCI3) delta: 8.00 – 7.91 (m, 2H), 7.66 – 7.58 (m, 2H), 7.33 – 7.27 (m, 1 H), 7.12 – 7.02 (m, 1 H), 4.42 (d, J = 7.8 Hz, 1 H), 3.25 – 3.1 1 (m, 1 H), 1.77 – 1.45 (m, 7H), 1.45 – 1.32 (m, 2H), 1.20 (s, 3H). LCMS: mobile phase A: 5 mM ammonium formate in water + 0.1 % ammonia, mobile phase B: acetonitrile + 5% mobile phase A + 0.1 % ammonia; Column: YMC Triart, C18 (50X4.6 mm) 3um; Flow rate: 1.4 mL/min. Run time: 4.5 mins – starting solvent 10:90 B:A is increased linearly to 95:5 B:A over the first 2.5 mins, held at 95:5 B:A for 0.5 min, reduced linearly to 10:90 B:A over 1 min and held at 10:90 B:A for the final 0.5 min. Retention time 2.53 min m/z 398[M-H].

According to the analysis of related databases, 327-52-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PIMCO 2664 LIMITED; SMITH, Stephen Allan; PATEL, Lisa; GREIG, Iain Robert; (91 pag.)WO2016/97001; (2016); A1;,
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. 10485-09-3, name is 2-Bromoindene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H7Br

Under an argon atmosphere, in a Schlenk flask,Followed by loading 3mmol of 2-bromoindene (Shanghai Bi Pharmaceutical Technology Co., Ltd.)1.5 mmol of 2,4,6-trimethylphenylboronic acid (Shanghai Bi Pharmaceutical Technology Co., Ltd.),3 mmol% of tetrakistriphenylphosphine palladium, 6 mmol% of S-Phos and 3 mmol of potassium phosphate,A mixture of 20 mL of toluene and 10 mL of water was added to dissolve the reaction. The reaction was carried out at 100 C for 24 hours,After cooling, the reaction mixture was extracted with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, the organic phase solvent was removed,Column chromatography on petroleum ether (Rf = 0.8) gave 2- (2,4,6-trimethylphenyl) indene,The yield is 90%

According to the analysis of related databases, 10485-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; University of Science and Technology of China; Xiao Bin; Zhou Qiaolan; Xu Mengyu; (22 pag.)CN107417723; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 460-00-4, name is 1-Bromo-4-fluorobenzene, 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 460-00-4, Recommanded Product: 460-00-4

Under nitrogen protection,Add carbazole (5 g, 30 mmol) to a 250 mL single-necked flask,P-fluorobromobenzene (10.47g, 60mmol),Cesium carbonate (21.5 g, 62 mmol) was mixed in dimethyl sulfoxide DMSO (100 mL).Reacted at 160 C for 48 hours,Cool to room temperature, extract with dichloro/water solution, and pass through the column with dichloromethane/petroleum ether.After drying in vacuo, 7.7 g of white crystals were obtained.The yield was 80%.

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

Reference:
Patent; Jilin University; Zhang Ming; Zhang Zhaoxia; (27 pag.)CN109988097; (2019); A;,
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. 4333-56-6, name is Bromocyclopropane, This compound has unique chemical properties. The synthetic route is as follows., name: Bromocyclopropane

Intermediate 54: (2S)-Lambda/-r(S)-cvclopropyl(phenv?methyll-3-methyl-1-r(trimethylsilyl)oxyl- 2-butanamine; EPO Cyclopropyl bromide (4.64g, 38.4mmole) was dissolved in dry Et2O (50ml) under argon, cooled to -780C and treated with tert-BuLi (45ml_ of a 1.7M solution in pentane, 76.5mmole). After 10 minutes, cooling was removed and the mixture stirred at room temperature for 1 hr. After re-cooling to -4O0C, a solution of Intermediate 52 (8.43g, 32mmole) in dry Et2O (40ml) was added and stirring continued at -4O0C for 1.5 hrs. 5M HCI acid was added (50ml) and the phases separated. The aqueous phase was washed with Et2O (discarded) and then basified with KOH pellets to pH >10 in the presence of Et2O. The organic phase was washed with water and brine and then evaporated to dryness under vacuum to afford the title compound as a colourless oil (6.42g, 86%); 1 HNMR (400MHz, CDCI3) delta 0.13 – 0.15, (1 H, m), 0.34 – 0.37, (2H1 m), 0.60 – 0.70, (1 H, m), 0.83, (3H, d, J = 7Hz), 0.91 , (3H, d, J = 7Hz), 0.98 – 1.00, (1 H, m), 1.71 – 1.77, (1 H, m), 2.44 – 2.48, (1 H, m), 3.00, (1 H, d, J = 8Hz), 3.32 and 3.36, (1 H, dd, J = 5 and 11 Hz), 3.59 and 3.61 , (1 H, dd, J = 5 and 11 Hz), 7.25 – 7.42, (5H, m); m/z(APCI): 234.2 [M+H]+.

According to the analysis of related databases, 4333-56-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/50992; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary