Tag: M.W=200-300

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. 4549-33-1

n-BuLi (1.63 M in hexane, 4.0 mL, 6.52 mmol) was added to a solution of iPr2NH (0.62 mL, 4.4 mmol) in tetrahydrofuran (THF) (5 mL) at 0C, and the whole mixture was stirred for 30 min at 0C. 3-Picoline (0.39 mL, 4.02 mmol) was added to the mixture at -78C, and the whole mixture was stirred for 20 min. Then, 1,9-dibromononane (2.43 mL, 12 mmol) was added to the mixture, and the whole mixture was gradually warmed to r.t. with stirring overnight. Sat. NaHCO3aq. was added to the reaction mixture, and the whole mixture was extracted with AcOEt. The combined organic layer was washed with brine and dried (Na2SO4). Removal of the solvent under reduced pressure to give a crude product, which was purified by SiO2 column chromatography (hexane-AcOEt=8 : 1) to give 5b(388 mg, 33%).1H-NMR (500 MHz, CDCl3) delta: 8.35-8.30 (2H, m), 7.39 (1H, d, J=7.7 Hz), 7.10 (1H, dd, J=7.7, 4.9 Hz), 3.30 (2H, t, J=6.9 Hz), 2.50 (2H, t, J=7.7 Hz), 1.74 (1H, quint, J=7.1 Hz), 1.53-1.48 (2H, m), 1.35-1.12 (12H, m). 13C-NMR (125 MHz, CDCl3) delta: 149.6, 146.8, 137.6, 135.5, 123.0, 33.8, 32.7, 32.5, 30.8, 29.11, 29.10, 29.07, 28.8, 28.4, 27.9. IR (KBr) cm-1: 2926, 2854, 1574, 1422, 1026. ESI-TOF-MS m/z: 298 (M+H)+. HRESI-TOF-MS m/z: 298.1163 (Calcd for C15H25NBr: 298.1170).

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:
Article; Arai, Masayoshi; Kamiya, Kentaro; Shin, Dayoung; Matsumoto, Hirokazu; Hisa, Tomoya; Setiawan, Andi; Kotoku, Naoyuki; Kobayashi, Motomasa; Chemical and Pharmaceutical Bulletin; vol. 64; 7; (2016); p. 766 – 771;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, 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 327-52-6, 327-52-6

Example 1: Preparation of (S)-1-chloro-3-(2,4,5-trifluorophenyl)propan-2-ol (formula 4) [Show Image] Preparation of 2,4,5-trifluorophenylmagnesium chloride solution: 700 mL of tetrahydrofuran was charged into reactor and cooled to 0 C, followed by the consecutive addition of 350 mL 2 M i-propylmagnesium chloride and 69 mL 1-bromo-2,4,5-trifluorobenzene applying stirring and maintaining temperature of the reaction mixture between 0 C and 5 C. After the addition, the reaction mixture was stirred gently for 1 h at 0 C to 5 C and for 3 h at 22 C obtaining the solution of 2,4,5-trifluorophenylmagnesium chloride.Determination of activity of the obtained solution: 0.25 g of iodine was weighed into small reaction flask and titrated with the solution obtained. When darkly brown solution turned its color to white suspension, the consumption of solution was ready. Typical consumption was about 1.85 mL/mmol of iodine.Conversion to compound of formula 4: To the whole amount of above prepared solution of Grignard reagent 28 mL of (S)-epichlorohidrin (formula 3) was added during stirring, followed by the addition of 0.80 g copper(I) chloride. Exotermic reaction started and when inner temperature raised to 40 C, external cooling was applied, lowering the internal temperature to 25 C. 28 mL of (S)-epichlorohidrin divided into two equal portions were added. After the addition, the reaction mixture was stirred for 5 h at 25 C, followed by the addition of 75 mL acetic acid and 750 mL methyl tert-butyl ether. The resulted mixture was washed consecutively with 700 mL water; mixture of 700 mL water, 80 mL brine, 80 mL 20% ammonium chloride, and 750 mL 2% sodium bicarbonate. Organic phase was evaporated at 60 C and 5 mbar, to yield 131 g of crude product of compound of formula 4 in the form of yellowish oil. 1H NMR (DMSO-d6): delta 2.64 (dd, 1H), 2.83 (dd, 1H), 3.49-3.64 (m, 2H), 3.85 3.90 (m,1H), 5.31 (d,1H), 7.37-7.48 (m, 2H).

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-Bromo-2,4,5-trifluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LEK Pharmaceuticals d.d.; EP2397141; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 7766-50-9, name is 11-Bromo-1-undecene, 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 7766-50-9, 7766-50-9

The absolute configuration of acetates 5 and 6 was confirmed by alternative chiral synthesis of (2S’,122)-2-acetoxy-12-heptadecene (6) using hydrolytic kinetic resolu- tion (HKR) as the key step (FIG. 6), as follows: 37.5 mmol of butyl lithium (15 ml of 2.5 M solution in hexane) was added under argon at -700C to 3.45 ml (30.0 mmol) of 1-hexyne (9) in 50 ml THF. After stirring 0.5 hours, 5 ml of HMPA and 1.8 ml (8.20 mmol) of 11-bromo-l-undecene (10) was added. The reaction mixture was then warmed to room temperature, stirred 24 hours, quenched with aq. NH4Cl, and extracted with hexane (2 x 50 ml). Combined extracts were washed with brine, dried (anh. MgSO4), and solvents evaporated. The crude product was filtered through 10 g of silica eluting with hexane, yielding 2.05 g of hydrocarbon 11 (85% pure by GC; 7.65 mmol). Without further purification compound 11 was treated with 13.1 mmol of r¡ã-chloroperoxybenzoic acid at 0C in 20 ml of dichloromethane. After 3 hours, the mixture was warmed to room temperature, and after a subsequent 30 min quenched with 50 ml of 2N NaOH and treated with 100 ml of ether. The organic layer was separated, washed with water and brine, and dried (anh. MgSO4). After filtration, removal of solvents in vacuo and flash chromatography, 0.82 g (87% pure by GC; 2.85 mmol) of unsaturated epoxide 12 was obtained. Epoxide 12 in 3 ml of dry THF with 0.030 ml of water was subjected to HKR with freshly prepared R,R-1 Jacobsen catalyst (7,8) [25 mg of (R,R)-N,NN -bis(3 ,5-di-tert-butylsalicylidene)-l ,2-cyclohexanediaminocobalt(II) (Aldrich Chemical Company, Milwaukee, WI) stirred 1 hour with 0.20 ml of toluene and 0.050 ml of acetic acid, and solvents removed in vacuo]. After stirring the reaction mixture 7 days, the recovered (R)-epoxide 13 was separated by flash chromatography [15 g of silica with hexanerether (80:20) as eluent] from the diol 14 and the catalyst, affording 0.4 g of 85% pure (R)-epoxide 13. After removal of solvents, 13 was dissolved in 2 ml of ether and added to a lithium aluminum hydride suspension (10 mmol) in 20 ml of ether. After stirring 3 hours, the reaction mixture was quenched with 2nu NaOH, and the organic phase removed and evaporated. The resulting acetylenic alcohol 15 was hydrogenated in 30 ml of hexane with Lindlar catalyst (5% palladium on calcium carbonate poisoned with lead, 100 mg) and 1 ml of quinoline, yielding 0.350 g of (25′,12Z)-2-hydroxy-12-heptadecene (4). Acetylation of 4, as described above, and further flash column purification gave 0.350 g (1.18 mmol) of (25,12Z)-2-acetoxy-12-heptadecene (6) (yield 14.5% based on 11-bromo-l-undecene 10) with 85% ee.

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, 11-Bromo-1-undecene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRIES, Regine; KHASKIN, Grigori; DAROOGHEH, Hassan; MART, Cafer; BRITTON, Robert; GRIES, Gerhard; WO2007/79563; (2007); 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. 626-40-4, name is 3,5-Dibromoaniline, This compound has unique chemical properties. The synthetic route is as follows., 626-40-4

(1) Preparation of diazonium salt: 100 1 ^ beaker by adding 5.011483, 5 dibromoaniline and 8 1 ^ 20% hydrochloric acid, 0 ~ 5 C slowly to the suspension by adding 1.5232 g of aqueous solution of sodium nitrite , The suspension becomes clear after adding urea to remove excess nitrous acid, sodium acetate solid to adjust the pH to 5, the clarified liquid set in ice water in reserve.(2) Preparation of o-methoxyanilide methanesulfonate:50 mL round bottom flask was added 10 mL of water and 2.3553 g sodium bisulfite, sodium bisulfite was dissolved and added 0.7221G paraformaldehyde, 60 C reaction 35 min after the drop of 2.4610 g o-methoxy aniline, after 2 h reaction to stop heating, o-methoxy anilino-methyl methanesulfonate mixture.(3) Preparation of azobenzene compound:After the mixture obtained in step (2) was cooled to room temperature, the mixture was slowly added dropwise to the diazonium salt obtained in the step (1), At this time, to clarify the diazonium salt solution gradually dark red viscous liquid, temperature control at 0 ~ 5 C reaction 6 h after the end of the reaction. Add 50 mL of 30% sodium hydroxide aqueous solution, dark red viscous liquid into yellow turbid liquid, nitrogen protection under 50 C hydrolysis 7 h, after the end of the reaction with hydrochloric acid to adjust the pH value of about 8, the crude product by thin layer chromatography , The dye: 0,5 & dibromo-3-methoxy-4-amino azobenzene 2.237g (yield 29%).

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; Lingnan Normal University; Song Xiumei; Feng Zongcai; (13 pag.)CN105001664; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

452-92-6, Name is 5-Bromo-2,4-difluoroaniline, 452-92-6, 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.

A solution of 2,4-difluoro-6-bromoaniline (5 g, 24 mmol), salicylaldehyde (2.5 mL, 24 mmol) and p-toluenesulfonic acid (14 mg, 0.07 mmol) in toluene (120 mL) was heated to reflux in a Dean-Stark apparatus for 2.5 h and then allowed to cool to ambient temperature. After adding triethylamine (1 mL) the reaction mixture was concentrated to give the crude title compound (7.3 g, 97%) which was used without further purification. 1H-NMR (400 MHz, CDCl3) 6.95-6.99 (m, 1H), 7.01-7.06 (m, 2H), 7.39-7.45 (m, 2H), 7.48-7.52 (m, 1H), 8.66 (s, 1H), 12.69 (s, 1H). (m/z)=312+314 (M+H)+.

Statistics shows that 5-Bromo-2,4-difluoroaniline is playing an increasingly important role. we look forward to future research findings about 452-92-6.

Reference:
Patent; N.V. Organon; US2008/90804; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

130723-13-6, 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 130723-13-6 as follows.

The 4-hydroxy-4-[3-(naphth-2-ylthio)-5-trifluoromethylphenyl]tetrahydropyran used as a starting material was obtained as follows: Sodium hydride (60% w/w dispersion in mineral oil; 0.5 g) was added portionwise to a mixture of 2-naphthalenethiol (1.42 g) and DMA (30 ml) and the mixture was stirred at ambient temperature for 1 hour. A solution of 1-bromo-3-fluoro-5-trifluoromethylbenzene (2.43 g) in DMA (10 ml) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine (50 ml), dried (MgSO4) and evaporated. The residue was purified by column chromatography using hexane as eluent. There was thus obtained 3-bromo-5-trifluoromethylphenyl 2-naphthyl sulphide (1.37 g, 40%), as an oil. A solution of the product so obtained in THF (10 ml) was cooled to -60 C. and n-butyl-lithium (1.6M in hexane; 2.3 ml) was added dropwise.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 130723-13-6, and friends who are interested can also refer to it.

Reference:
Patent; Imperial Chemical Industries; ICI Pharma; US5208259; (1993); A;,
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. 4549-33-1, name is 1,9-Dibromononane, A new synthetic method of this compound is introduced below., 4549-33-1

General procedure: Finely ground KOH(4.48 g, 80 mmol) was added to a solution of pyrazole(2.72 g, 40 mmol) in DMSO (20 ml). The suspension wasthoroughly stirred for 30 min at 80, then treated bydropwise addition of 1,4-dibromobutane (4.32 g, 2.41 ml,20 mmol) in DMSO (10 ml) over 30 min, while cooling thereaction mixture with water. After finishing the addition ofdibrom derivative, stirring and heating at 80 wascontinued for additional 4 h, the reaction mixture wasthen poured into water (200 ml), extracted withchloroform (5¡Á10 ml), the extract was washed one timewith distilled water (10 ml) and dried over anhydrousCaCl2. Chloroform was removed by distillation undervacuum.

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:
Article; Zatonskaya, Lina V.; Schepetkin, Igor A.; Petrenko, Tatiana V.; Ogorodnikov, Vladimir D.; Khlebnikov, Andrei I.; Potapov, Andrei S.; Chemistry of Heterocyclic Compounds; vol. 52; 6; (2016); p. 388 – 401; Khim. Geterotsikl. Soedin.; vol. 52; 6; (2016); p. 388 – 401,14;,
Bromide – Wikipedia,
bromide – Wiktionary

40161-54-4, 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. 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below.

General procedure: Benzimidazole (5 mmol), 1-bromo-2-fluorobenzene derivatives (15 mmol, 2 equiv) and tripottasium phosphate (5.31g, 25 mmol, 5 equiv) were dissolved in DMF (30 mL). The mixture was stirred at 150 C. The reaction time was determined by monitoring with TLC. The reaction mixture was diluted with CH2Cl2 (50 mL) and water (50 mL). The phases were separated, and the aqueous layer was extracted with CH2Cl2 (2 ¡Á 30 mL). The combined organic layerswere washed with water (3 ¡Á 50 mL), dried with MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/AcOEt).

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; Matsumura, Mio; Kitamura, Yuki; Yamauchi, Arisa; Kanazawa, Yoshitaka; Murata, Yuki; Hyodo, Tadashi; Yamaguchi, Kentaro; Yasuike, Shuji; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 2029 – 2035;,
Bromide – Wikipedia,
bromide – Wiktionary

5003-71-4, 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. 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide, This compound has unique chemical properties. The synthetic route is as follows.

TERT-BUTYL N-(3-BROMOPROPYL)CARBAMATE: was prepared from 3-bromopropylamine hydrobromide and BOC2O in the presence of base in dichloromethane.

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; Synaptic Pharmaceutical Corporation; US6727264; (2004); 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. 2606-51-1, name is 5-(Bromomethyl)benzo[d][1,3]dioxole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 2606-51-1

General procedure: The mixture of N-hydroxyhept-6-ynamide (141 mg, 1 mmol), benzyl bromide (256 mg, 1.5 mmol), sodium azide (98 mg, 1.5 mmol), copper(II) sulfate pentahydrate (38 mg, 0.13 mmol), sodium ascorbate (60 mg, 0.3 mmol) in wate and tert-butanol (v/v = 1:1, 10ml) was heated to 66 oC, the heterogeneous mixture was stirred vigrously for 24 h. After addition of water (50 ml), the mixture was filtered. The filter cake was dissloved in MeOH (20 ml), the insolubles was filtered, the filtrate was concentrated in vacuo and crystallized in ethyl acetate to give 2 (156 mg, 57%) as a white solid.

The synthetic route of 2606-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Qiao; Yao, Yiwu; Liu, Chunping; Li, Hua; Yao, Hequan; Xue, Xiaowen; Liu, Jinsong; Tu, Zhengchao; Jiang, Sheng; Bioorganic and Medicinal Chemistry Letters; vol. 23; 11; (2013); p. 3295 – 3299;,
Bromide – Wikipedia,
bromide – Wiktionary