Tag: M.W=100-200

Synthetic Route of 58534-95-5,Some common heterocyclic compound, 58534-95-5, name is 3-Bromo-2-fluoroaniline, molecular formula is C6H5BrFN, 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.

General procedure: GP3-1: A solution of 2-halo substituted aniline (1.0 eq), potassium ethyl xanthate (1.2 eq or 2.2 eq,typically 2.2 eq) in 10 volume of anhydrous DMF was heated at 100 0Cor 120 0C for 4 hours under nitrogen. TLC monitored the progress ofreaction. After completion, the reaction mixture was cooled to room temperature,diluted with water (10 volume) and neutralized by 1 M HCl solution to pH 5. Theformed precipitate was collected by filtration, rinsed with water, firstlydried by rotavapor, and then dried by oil pump to afford 2-mercaptobenzothiazole.GP3-2: 2-mercaptobenzothiazole in 10 volume ofanhydrous DCM, was added by sulfuryl chloride (SO2Cl2, 1volume) under ice-cooled condition. The mixture was stirred at rt for 1 hour,which was monitored by TLC. After consumption of starting material, the mixturewas diluted by 30 volume of ether, following quenching carefully by addingwater. Stirring was kept for 1 hour to make sure the SO2Cl2was totally consumed and product was released. Organic layer was collected,neutralized by saturated NaHCO3, dried over Na2SO4and purified by silica gel chromatograph to give the pure product, which wasfinally characterized by LC-MS and NMR.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-2-fluoroaniline, its application will become more common.

Reference:
Article; Lv, Fengping; Li, Zhi-Fang; Hu, Wenhao; Wu, Xiaohua; Bioorganic and Medicinal Chemistry; vol. 23; 24; (2015); p. 7661 – 7670;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 38573-88-5, 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. 38573-88-5 name is 1-Bromo-2,3-difluorobenzene, 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 48 2-Trifluoroacetamido-3-phenyl-6-(2,3-difluorobenzoyl)-imidazo[1,2-a]pyridine To a solution of 2,3-difluorobromobenzene (471 ml, 4.206 mmol) in dry THF (20 mL) was added a solution of n-butyl lithium (1.6M in hexanes, 2.63 mL) at -78¡ã C. The resulting yellow solution was stirred at the same temperature for 70 minutes, then a solution of 2-trifluoroacetamido-3-phenyl-6-(N-methyl-N-methoxycarbamoyl)imidazo[1,2-a]pyridine (0.500 g, 1.28 mmol) in dry THF (20 mL), was added dropwise via a cannula. The red-orange solution was allowed to warm over 60 minutes. Saturated NH4Cl was added and the mixture was stirred for 25 minutes before extracting with EtOAc. The organic layer was washed with brine, dried (Na2SO4), concentrated in vacuo and purified by column chromatography (CH2Cl2/CH3CN 4/1) to give 390 mg of an orange solid. (69percent). MS(FAB), NMR.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,3-difluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; US6358971; (2002); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 2695-48-9, name is 8-Bromo-1-octene, 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 2695-48-9, HPLC of Formula: C8H15Br

2-(2-(2-methoxyethoxy)ethoxy)ethanol (0.516 g, 3.140 mmol, 1.2 equiv) and NaH (0.220 g, 9.157 mmol,3.5 equiv) were dissolved in dry THF (10 mL). After 15 min stirring, 8-bromooct-1-ene (0.50 g, 2.616mmol, 1 equiv) was added. The mixture was stirred for 12 hours under nitrogen at 65 C. After solventevaporation, the crude product was purified by flash chromatography (Petroleum Ether/ EtOAc 8:2).0.317 g (48%) of III were obtained. 1H NMR (500 MHz, CDCl3) delta 5.88 – 5.69 (m, 1H, CH), 5.06 – 4.82 (dd, 2H, CH2), 3.67 – 3.60 (m, 8H, CH2O),3.56 (m, J = 5.9, 3.8 Hz, 2H, CH2O), 3.53 (m, J = 5.7, 3.7 Hz, 2H, CH2O), 3.43 (t, J = 6.8 Hz, 2H, CH2O), 3.36(s, 3H, CH3O), 2.07 – 1.98 (m, 2H, CH2), 1.60 – 1.51 (m, 2H, CH2), 1.41 – 1.25 (m, 6H, CH2). 13C NMR (126 MHz, CDCl3) delta 139.20 (1C, CH2), 114.08 (1C, CH), 71.91 (1C, CH2O), 71.42 (1C, CH2O),70.60 (1C, CH2O), 70.57 (1C, CH2O), 70.49 (1C, CH2O), 70.03 (1C, CH2O), 58.99 (1C, CH3O), 33.68 (1C,CH2), 29.55 (1C, CH2), 28.91 (1C, CH2), 28.82 (1C, CH2), 25.91 (1C, CH2).ESI-MS (m/z): 275.2 [M+H+], 297.2 [M+Na+].

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, 8-Bromo-1-octene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Riccardi, Laura; Gabrielli, Luca; Sun, Xiaohuan; De Biasi, Federico; Rastrelli, Federico; Mancin, Fabrizio; De Vivo, Marco; Chem; vol. 3; 1; (2017); p. 92 – 109;,
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. 2550-36-9, name is (Bromomethyl)cyclohexane, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H13Br

2,6-dihydroxy acetophenone solution (2,6-dihydroxyacetophenone, compound 7, 1.0 eq.), Anhydrous potassium carbonate (anhydrouspotassium carbonate, 2.0 eq.), Dissolved in acetone, alkyl bromide mixture (alkyl bromides, 1.0 eq.) Were mixed and it reacted for 18 hours at 70 ~ 80 . After evaporation of acetone, the remaining reaction product was diluted with dichloromethane and washed three times in water. The organic layer was then collected and concentrated under reduced pressure and then dehydrated with anhydrous Na2SO4 and the crude product obtained by separating the crude product was purified by column chromatography to obtain a compound 9a ~ 9d.

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 2550-36-9.

Reference:
Patent; Chungnam National University Industry-Academic Cooperation Foundation; Chungbuk National University Industry-Academic Cooperation Foundation; Jung, Sang Hun; Kim, Young Soo; (39 pag.)KR101535119; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 4117-09-3, A common heterocyclic compound, 4117-09-3, name is 7-Bromo-1-heptene, molecular formula is C7H13Br, 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.

General procedure: Coupling of Alkyl Halides with t-BuMgCl; Procedure 1 (P1)An alkyl halide (1.0 mmol), decane (63 mg as an internal standard)and LiI (5.3 mg, 0.04 mmol) were added to a dry, nitrogen-flushedtest tube equipped with a rubber septum and a magnetic stir bar.THF (0.8 mL) was added and the solution was cooled to -78 C usinga dry ice/EtOH bath. t-BuMgCl (2a) (1.5 mL, 0.81 M in THF,1.2 mmol) was added slowly followed by isoprene (136.2 mg, 2.0mmol). To this mixture was added CoCl2 [2.6 mg, 0.02 mmol, as apowder or as a THF solution (0.5 mL, 0.04 M)]. (Note 1: CoCl2should be added after isoprene, otherwise the catalytic performancedecreases significantly). The cold bath was removed and the mixturewas warmed to r.t. (ca. over 10 min), and then heated for 5 h bysuspending the reaction vessel in an oil bath kept at 50 C. (Note 2:when the reaction mixture was heated at 30 C during this stage, unidentifiedside reactions occurred resulting in low yields of couplingproducts). The resulting mixture was cooled to 0 C in an ice bathand the reaction was quenched with aq HCl (5 mL, 1 M). The productwas extracted with Et2O (3 ¡Á 20 mL). The combined organiclayer dried over Na2SO4, concentrated and analyzed by gas chromatographyto determine the GC yield. The residue was purified by silicagel column chromatography or by GPC. According to P1, 7-bromohept-1-ene (4b) (177 mg, 1.0 mmol) andt-BuMgCl (2a) (0.81 M in THF, 1.2 mmol) were reacted under standardconditions.Yield: 86% (determined by GC using decane as an internal standard).

The synthetic route of 4117-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Iwasaki, Takanori; Takagawa, Hiroaki; Okamoto, Kanako; Singh, Surya Prakash; Kuniyasu, Hitoshi; Kambe, Nobuaki; Synthesis; vol. 46; 12; (2014); p. 1583 – 1592;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 3814-30-0, 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. 3814-30-0, name is (Bromomethyl)cyclopentane, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 2-(4-(ethylsulfonyl)phenyl)-N-(4-((propylamino)methyl)phenyl)acetamide (50 mg, 0.13 mmol) was added sequentially to a 20 mL sealed tube.2-chlorobenzyl bromide (53 muL, 0.4 mmol),Anhydrous potassium carbonate (55 mg, 0.4 mmol),N,N-dimethylformamide 2mL,Heated at 60 C for 3 hours,TLC confirmed that the reaction was completed and washed with saturated brine.Purification of petroleum ether by column chromatography: ethyl acetate 2:1?3:2,Made a white solid 18mg,The yield was 27.8%.

The chemical industry reduces the impact on the environment during synthesis (Bromomethyl)cyclopentane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Fudan University; Wang Yonghui; Qiu Ruomeng; Gong Juwen; Tian Jinlong; Huang Yafei; (65 pag.)CN109206346; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1003-99-2, 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. 1003-99-2, name is 2-Bromo-5-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 1; Synthesis of l-ethyl-3-[4-fluoro-7-(3-fluoropyridin-2-yl)-5-(pyridin-3-yl)-l,3- benzothiazol-2-yl]urea (Compound No. 1); Step 1 : Synthesis of N-(2-bromo-5-fluorophenyl)-2,2-dimethylpropanamide :; To a solution of 2-bromo-5-fluoroaniline (15.0 g, 85.7 mmol) in dichloromethane (120 mL) were added triethylamine (11.25 g, 110.0 mmol) followed by pivaloyl chloride (11.3 g, 92.0 mmol) drop-wise at 0 0C and then stirred at 25-30 0C for about 4 hours. The reaction mixture was diluted with dichloromethane and washed with saturated solution of sodium bicarbonate followed by water. The organic layer was dried over anhydrous sodium sulfate, filtered and then concentrated to give the crude residue, which was purified through column chromatography using silica gel 230-400 mesh size and eluted with 5percent ethyl acetate in hexane to yield the title compound (20 g)

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-5-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2009/156966; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 111721-75-6, A common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, molecular formula is C6H5BrFN, 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.

To a stirred solution of 2-bromo-3-fluoroaniline (5.00 g, 26.3 mmol) in dry THF (50 mL) at 0 C under nitrogen atmosphere was added pyridine (3.18 mL). Then 3- chloropropanoyl chloride (3.02 mL g, 31.6 mmol) was added in dropwise carefully. Then the reaction mixture was warmed to room temperature and stirred for 16 hours. After that the reaction mixture was concentrated under reduced pressure. The residue obtained was diluted with water (100 mL) and extracted with ethyl acetate (3 x 75 mL). The combined extract was washed with water, brine, dried over Na2S04 and concentrated in vacuo to get compound Xa (crude), which was used for the next step without any further purification. Yield: 6.40 g; -NuMuIota (400 MHz, DMSO-d6): 9.77 (s, 1H), 7.48 – 7.39 (m, 2H), 7.24 – 7.19 (m, 1H), 3.88 (t, = 6.4 Hz, 2H), 2.91 (t, = 6.4 Hz, 2H)

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; BUGWORKS RESEARCH INDIA PVT LTD; PEER MOHAMED, Shahul Hameed; BHARATHAM, Nagakumar; KATAGIHALLIMATH, Nainesh; SHARMA, Sreevalli; NANDISHAIAH, Radha; RAMACHANDRAN, Vasanthi; VENKATARAMAN, Balasubramanian; (221 pag.)WO2018/225097; (2018); 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. 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

4-(6-Chloro-4-(ethoxycarbonyl)chroman-7- yloxy)benzoic acid (Preparation 1) (0.214 g, 0.569 mmol) was dissolved in 1,2- dichloroethane (2 ml) and a drop of DMF was added. To the mixture was added oxalyl chloride (2M in dichloromethane) (0.313 ml, 0.626 mmol). Gas evolution was observed. The mixture was stirred for 2 hours at ambient temperature. A solution of 3-bromo-4- fluoroaniline (0.113 g, 0.597 mmol) and triethylamine (0.158 ml, 1.138 mmol) in dichloromethane (1 ml) was added to the acid chloride solution. The mixture was stirred for 0.5 hour and the crude mixture was purified on silica gel (EtOAc in hexanes gradient) to provide 0.2656 g of the title compound as a white solid (85%).

The synthetic route of 656-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2009/158426; (2009); 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. 586-61-8, name is 1-Bromo-4-isopropylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H11Br

A mixture of 30.0 g (0.20 mol) of 2-FORMYLPHENYLBORONIC acid, 43.8 g (0. 22 MOL) of 4-bromoisopropylbenzene, 91.0 g (0.60 mol) of caesium fluoride and 6.9 g (0.0060 mol) of tetrakis (triphenylphosphine) palladium (0) in 700 ml of 1,2-dimethoxyethane is refluxed under a nitrogen atmosphere for 3 hours. After cooling, 1.5 1 of diethyl ether and 1 1 of water are added to the reaction medium and the organic phase is separated out, dried over sodium sulfate and concen- trated. The oily residue obtained is purified by chromatography on a column of silica (eluent : 30/1 hexane/ethyl acetate) to give 25.3 g (56.4%) of a pale yellow oil corresponding to the title compound. NMR: (CDCI3) 8 (PPM) : 1.31 (6 H, d, J = 7 Hz); 2.99 (1 H, sept, J = 7 Hz); 7.26-7. 39 (4 H, m); 7.41-7. 53 (2 H, m); 7.54-7. 69 (1 H, m); 7.93-8. 13 (1 H, m); 10. 01 (1 H, s). I R : v (C =0) : 1694 CM~

According to the analysis of related databases, 586-61-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; WO2004/37806; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary