Category: bromides-buliding-blocks

Electric Literature of 74586-53-1,Some common heterocyclic compound, 74586-53-1, name is 3-Bromo-5-methylaniline, molecular formula is C7H8BrN, 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: The amino phenyl derivative (0.4 mmol, 1 equiv) was dissolvedin pyridine absolute (3 mL) and was spiked with sulfonyl chloride/acid chloride (1.5 equiv). The reaction mixture was stirred overnightat rt (refluxed in case of amide coupling). The reaction wasquenched by adding 10 mL of 2 N HCl and extracted with ethylacetate (3 50 mL). The organic layers werewashed with saturatedNaHCO3 (50 mL) and brine (50 mL), dried over magnesium sulfate,filtered and concentrated to dryness. The product was purified byCC. Thetitle compound was prepared by reaction of 3-bromo-5-methylaniline (1000 mg, 5.38 mmol, 1 equiv) andcyclopropanesulfonyl chloride (1013 mg, 8.07 mmol, 1.5 equiv) according to MethodC. The product was purified by CC (hexane/ethyl acetate 8:2); yield: 77% (1200mg). 1H NMR (500 MHz, acetone-d6) delta 8.62 (br. s, 1H), 7.35 (s, 1H), 7.15(s, 1H), 7.13 (s, 1H), 2.65-2.61 (m, 1H), 2.30 (s, 3H), 1.00-0.95 (m, 4H).

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-5-methylaniline, its application will become more common.

Reference:
Article; Abdelsamie, Ahmed S.; Bey, Emmanuel; Gargano, Emanuele M.; Van Koppen, Chris J.; Empting, Martin; Frotscher, Martin; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 56 – 68;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 52997-43-0, name is 7-(Bromomethyl)pentadecane, 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 52997-43-0, Formula: C16H33Br

The aqueous NaOH solution (13.5 ml, 6 M) was placed in a reaction flask,Ventilation (nitrogen) three times,A solution of p-bromophenethyl mercaptan (9.77 g, 45 mmol) was added dropwise under nitrogen,After dripping,The phase transfer catalyst was added tetrabutylammonium iodide (catalyst amount, 1.99 g).Ten minutes later, 61 ml of tetrahydrofuran was added,To be uniform,Ethyl 2-hexyl decane (16.50 g, 54 mmol) was added dropwise over 10 min.The temperature was then raised to 45 C,The reaction was stirred overnight under vigorous stirring.Reaction is completed,The reaction solution was poured into dilute hydrochloric acid (1 M)Extracted with dichloromethane,Dried over anhydrous sodium sulfate,The solvent was distilled off under reduced pressure,The column was crystallized from 16.3 g of a colorless transparent liquid in 85% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-(Bromomethyl)pentadecane, and friends who are interested can also refer to it.

Reference:
Patent; Beijing Institute of Printing; Wang, Wenguang; Yang, Mingcong; Pu, Jialing; (29 pag.)CN104961665; (2017); B;,
Bromide – Wikipedia,
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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. 656-64-4, name is 3-Bromo-4-fluoroaniline, A new synthetic method of this compound is introduced below., Formula: C6H5BrFN

4-Amino-N-hydroxy-1,2,5-oxadiazol-3-methylimidoyl chloride (36.78 g, 0.23 mol, 1.0 eq)Dissolved in water (318 ml), stirred at 60 C, and added 3-bromo-4-fluoroaniline (47.50 g, 0.25 mol, 1.1 eq).Stir at 60 C for about 10 min,NaHCO3 (29.40 g, 0.35 mmol, 1.5 eq) in water (318 mL) was added dropwiseThe solution was added dropwise after 20 minutes, and the mixture was stirred at 60 C for 30 min, cooled to room temperature, and the reaction solution was suction filtered.The filter cake was washed with water, the filter cake was drained, beaten with water overnight, and filtered by suction the next day to obtain a gray solid, which was dried.The objective product was obtained (61.21 g, yield: 84.2%).

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; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Li Lin; (48 pag.)CN108727361; (2018); A;,
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. 2695-48-9, name is 8-Bromo-1-octene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 8-Bromo-1-octene

15.(1) Synthesis of p-(7-octenyloxy)benzoic acid 9.4 g of 8-bromo-1-octene, 9.0 g of ethyl p-hydroxybenzoate, and 7.6 g of potassium carbonate were refluxed in ethanol for 10 hours. Added thereto was an aqueous solution containing 2.4 g of sodium hydroxide, and reflux was further continued for 10 hours. After conclusion of the reaction, the reaction solution was diluted with water, and the pH of the diluted solution was lowered to 2 by dropping hydrochloric acid thereto. The generated precipitate was collected, and was then washed with water sufficiently and dried, to obtain 10.8 g of the objective ether compound. (Yield: 89 %)

The synthetic route of 2695-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDEMITSU KOSAN COMPANY LIMITED; EP355772; (1991); A3;,
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. 630-17-1, name is 1-Bromo-2,2-dimethylpropane, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H11Br

A mixture of 4,5,6,7-tetrahydro-1H-benzo[d]imidazole (5.00 g, 40.9 mmol),90% KOH (3.74 g, 60 mmol) and DMSO (70 mL) was stirred under argon and heated at 40 C for 2 h. After cooling to 10 C, neopentyl bromide (5.5 mL, 44 mmol) was added in one portion, and the resulting mixture was stirred and heated at 40 C for 4 days. The reaction mixture was poured into ice/water (800 mL), treated with 5 NNaOH (200 mL), and extracted with DCM (2 x 400 mL). The extract was washed with water (200 mL), dried over Na2SO4, and the solvent was removed under reduced pressure to give a residue. Column chromatography of the residue (silica gel, ethyl acetate/methanol, 95:5) afforded pure 1-neopentyl-4,5,6,7-tetrahydro-1H- benzo[d]imidazole (4.72 g, 60% 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; NITTO DENKO CORPORATION; STANISLAW, Rachwal; HU, Yufen; ZHANG, Hongxi; WANG, Peng; (42 pag.)WO2018/191238; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 33070-32-5, 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. 33070-32-5 name is 5-Bromo-2,2-difluorobenzodioxole, 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.

A 250 mL round bottom flask with stir bar was charged with toluene (100 mL), and the solvent was sparged with N2 for one hour. Trisodium phosphate (20.75 g, 127 mmol) was added, followed by bis(dibenzylideneacetone)palladium (0.970 g, 1.68 8 mmol). A solution of tri-tert-butylphosphine (0.683 g, 3.38 mmol) was added over 10 minutes via syringe, and the suspension was stirred for 50 minutes at 25C. 5-Bromo-2,2-difluorobenzo[dj[1,3jdioxole (10 g, 42.2 mmol) was added, and after stirring for 50 minutes at 25 C, ethyl 2-cyanoacetate (9.55 g, 84 mmol) was added over 5 minutes, followed by the addition of 1.5 mL of water. The reaction was heated at 75 C for 12 hours. Three additional vials were set up as described above. After completion of the reaction, all four reaction mixtures were combined. The reaction was cooled to 25 C and filtered over diatomaceous earth. The filtrate was concentrated, and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 5/1) to provide the title compound (24.5 g, 48.5 % yield). ?H NMR (400 MHz, DMSO-d6) 6 ppm 1.15 – 1.23 (m, 3 H) 4.13 – 4.29 (m, 2 H) 7.30 (dd, J=8.38, 1.76 Hz, 1 H) 7.46 – 7.55 (m, 2 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2,2-difluorobenzodioxole, and friends who are interested can also refer to it.

Reference:
Patent; ABBVIE S.A.R.L.; GALAPAGOS NV; CHAN, Vincent S.; KYM, Philip R.; SHEKHAR, Shashank; WANG, Xueqing; (89 pag.)WO2018/116185; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 4549-33-1, 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 4549-33-1 as follows.

General procedure: Furanchalcone or quinoline (1 mmol), potassium hydroxide(1.5 mmol, 84.2 mg) and acetonitrile (10 mL), were placedin a 25 mL flat-bottomed flask equipped with a magneticstirring bar. The mixture was stirred and heated to reflux fora period of 5 min, under microwave irradiation. Then, 1,omega-dibromoalkane (1.1 mmol) was added to the reaction mixture,which was refluxed for 30 min (200 W). The crudereaction mixture was concentrated on a rotatory evaporatorand the residue was purified by column chromatographyover silica gel eluting with hexane and a mixture of hexaneethylacetate (9:1 ratio) to obtain bromoalkyl derivatives inyields ranging between 61 and 76%. Monitoring of thereaction progress and product purification was carried outby TLC.

According to the analysis of related databases, 4549-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Garcia, Elisa; Coa, Juan C.; Otero, Elver; Carda, Miguel; Velez, Ivan D.; Robledo, Sara M.; Cardona, Wilson I.; Medicinal Chemistry Research; vol. 27; 2; (2018); p. 497 – 511;,
Bromide – Wikipedia,
bromide – Wiktionary

39478-78-9, name is 5-Bromo-2-methylaniline, 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. Recommanded Product: 39478-78-9

Compound W (270 mg, 0.84 mmol), 5-bromo-2-methylaniline (93.3 mg, 0.5 mmol),Cesium carbonate (407.3,1.25mmol), Pd2 (dba) 3 (22.9mg, 0.025mmol),213697-53-1 (15.7 mg, 0.04 mmol) was placed in a flask, acetonitrile (3 ml) was added, nitrogen was purged three times, and refluxed for 5 h.Cooled to room temperature, concentrated under reduced pressure, diluted with water and extracted twice with ethyl acetate. The organic phases were combined and washed with saturated brine.After drying over anhydrous sodium sulfate, it was concentrated and purified by silica gel column (PE:EA=1:1) to obtain 135 mg of pale yellow viscous compound K, yield: 71.6%.

The synthetic route of 39478-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University; Yu Jiang; Chen Yuanwei; (26 pag.)CN107814785; (2018); A;,
Bromide – Wikipedia,
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945244-29-1, name is 5-Bromo-2-fluoro-4-methylaniline, 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. SDS of cas: 945244-29-1

Method B: To 4 necked round bottom flask, equipped with mechanical agitation, thermometer, and N2 inlet is added 5-bromo-2-fiuoro-4-methylaniline (200g, 0.98 mol), CH3COOK (192g, 1.95 mol, 2.0eq), bis(pinacolato)diboron (248g, 0.98 mol,1.0eq) and IPAC (3L). After degassing with N2 for 30 min, the mixture is warmed to 50C and Pd(dppf)Cl2 (8g, 4wt%) is added. The reaction mixture is heated under reflux for at least lOh until the content of starting material <2% (GC). The mixture is cooled to 20~30C, filtered through a pad of Celite and rinsed with IPAC (1L). The filtrate is concentrated to 400~500ml remaining. The residue is mixed with n-Heptane (700ml), filtered through a Si02 pad and eluted with IPAC/n-Heptane(l/5 first, ~2L, and then 2/5, ~3L ). The filtrate is concentrated to 350~400ml. n-Heptane (300ml) is added and the mixture is again concentrated to 350~400ml. The residue (suspension) is cooled to -10- -20C and filtered after stirring for 2- 5 h. The crude product is dissolved in MeOH (200 ml) at 30-40 C, then slowly add H20 (600 ml) dropwise in 0.5~lh. The suspension is cooled to 20-30 C and filtered after stirring for 1-2 h .The solid is dried under high vacuum to afford the title compound as off- white solid (183g, 74% yield and 99% purity detected by UV absorption at 210 nm; 1H NMR (400 MHz, CDC13): delta 7.42 (d, J = 10.2 Hz, 1H), 7.01 (d, J = 12.4 Hz, 1H), 3.76 (s, 2H), 2.64 (s, 3H), 1.55 (s, 12H); 13C NMR(500MHz,CDC13): delta 20.66, 20.67, 24.40, 82.93, 116.20, 124.37, 130.64, 135.02, (151.93, 153.37);19F NMR (400 MHz,CDC13): delta 145.72 The synthetic route of 945244-29-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; ELI LILLY AND COMPANY; DECIPHERA PHARMACEUTICALS, LLC; ALLGEIER, Matthew Carl; FLYNN, Daniel L.; KAUFMAN, Michael D.; PATEL, Phenil J.; WOLFANGEL, Craig D.; WO2013/134243; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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, Computed Properties of C6H2Br2F2

(3-3) Synthesis of Compound L3 (0072) Bis(triphenylphosphine)palladium(II) dichloride [Pd(PPh3)2Cl2](0.12 g, 0.17 mmol) and Compound L3-1 (1.5 g, 5.5 mmol) were placed in a reaction flask. Then, lithium chloride (1.4 g, 33.1 mmol), Compound L3-2 (6 g, 16.6 mmol), and 40 ml of anhydrous toluene were added to the reaction flask to obtain a mixture. The mixture was heated under reflux for 3 days. Next, the temperature of the mixture was slowly reduced to 20° C., and the mixture was filtered using celite to remove side products and to collect a filtrate. The solvents in the filtrate was removed, and then the filtrate was washed several times with ethyl acetate and with a saturated sodium chloride aqueous solution to collect an organic layer. The organic layer was dehydrated using sodium sulfate (Na2SO4) to obtain a crude product. The crude product was subjected to column chromatography (SiO2, ethyl acetate:n-hexane=1:3), followed by recrystallization in a mixed solvent having dichloromethane and n-hexane (dichloromethane:n-hexane=1:1) at 20° C., thereby obtaining transparent crystals (780 mg, 53percent yield). (0073) The spectrum analysis for the transparent crystals is: 1H NMR (400 MHz, d6-acetone): delta 8.84 (t, J=6.8 Hz, 1H), 8.74 (d, J=4.8 Hz, 2H), 7.947.87 (m, 4H), 7.417.38 (m, 2H), 7.29 (t, J=9.4 Hz, 1H); 19F NMR (376 MHz, d6-acetone, decouple H, 298 K): delta ?112.95. The transparent crystals were confirmed to be Compound L3 having a chemical structure represented by

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; NATIONAL TSING HUA UNIVERSITY; Chi, Yun; Tong, Bi-Hai; Duan, Tai-Nan; Ku, Hsiao-Yun; Chen, I-Jen; US9219237; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary