Month: December 2020

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. 10016-52-1, name is 2,8-Dibromodibenzo[b,d]furan belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 10016-52-1

Dibromodibenzo [b, d] furan (1.0 g, 3.07 mmol, 1.0 eq) was dissolved in tetrahydrofuran (35 ml) followed by the addition of Tetrahydrofuran To a 25 ml flaskThe mixture was gradually added at 45 and stirred. After completion of the reaction, the reaction mixture was distilled under reduced pressure to remove the solvent. The solvent was distilled off (100 ml X 3), and the filtrate was dried over MgSO 4, filtered, and dried to obtain dibenzo [b, d] furan-2,8-diylbis ) Phenyl) methanol (1.7 g). The solution was dissolved in 35 ml of methanol and 35 ml of hydrogen chloride, followed by heating and stirring at 80 C for 2 hours. After the reaction was completed, the solvent was distilled off to remove the solvent, and then a small amount of distilled water was added thereto. After the work-up, water was removed with MgSO 4 and filtered to obtain G-4 (1.3 g, yield 63.17%

The synthetic route of 10016-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Korea Jiao Tong University Academic Cooperation; Lee, Ji Hun; Choe, Sung Hyun; Yun, Poo Yong; Yun, Moo Sang; (25 pag.)KR101638767; (2016); B1;,
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

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

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. 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 955959-84-9

In the argon atmosphere, weighing intermediate respectively (1-1) 3.2g (10.0mmol), intermediate (A-2-1) 5.8g (10.0mmol), Pd2(dba)30.14g (0.15mmol), P (tBu)3HBF40.087g (0.3mmol), tertiary butyl alcohol sodium 1.9g (20.0mmol), adding anhydrous xylene 50 ml, heating reflux for 8 hours.After the reaction, the reaction mixture is cooled to 50 ¡ãC, filtered through diatomaceous earth/silica gel, concentrated filtrate. The obtained concentrated residue after being refined with silica gel column chromatography, using toluene recrystallization, get 2.9g of the white crystal (yield 35percent).

The synthetic route of 955959-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; Jiateng, Pengxi; Sounei, Shenhao; Zhou, Qiaozhenghe; Tengshan, Gaoguang; (107 pag.)CN105431417; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

586-61-8, 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. 586-61-8 name is 1-Bromo-4-isopropylbenzene, 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.

General procedure: n-BuLi (1.55 M solution in hexane, 2.32 mL, 3.6 mmol) was added dropwise to a solution of 4-methylphenyl bromide (513 mg, 3.0 mmol) in THF (6.0 mL) at -50 C under Ar atmosphere. After 30 min, DMF (278 muL, 3.6 mmol) was added and the obtained mixture was gradually warmed to r.t. After 1 h at the same temperature, NH2OHxHCl (313 mg, 4.5 mmol) and K2CO3 (622 mg, 4.5 mmol) were added and the obtained mixture was stirred for 2 h at r.t. Then, after removal of the solvent under reduced pressure, toluene (3.0 mL), DPPA (1.61 mL, 7.5 mmol), and DBU (1.57 mL, 10.5 mmol) were added to the obtained residue under Ar atmosphere. After being stirred for 16 h under refluxing conditions, the mixture was cooled to r.t. and then, saturated NaHCO3 aq. (15.0 mL) was added. After being stirred for 5 min, the mixture was diluted with water (5.0 mL). The aqueous layer was then washed with AcOEt (25.0 mL) and acidified with 1.0 M HCl aq. to pH 2. The aqueous layer was extracted with AcOEt (2 x 25.0 mL). Removal of the solvent, followed by purification of the residue by short column chromatography on neutral silica gel (AcOEt: hexane = 1:3-1:1) gave 5-(4?-methylphenyl)tetrazole 3A (336.1 mg, 70%).

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

Reference:
Article; Kobayashi, Eiji; Togo, Hideo; Tetrahedron; vol. 74; 31; (2018); p. 4226 – 4235;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 1575-37-7, name is 4-Bromobenzene-1,2-diamine, molecular formula is C6H7BrN2, 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. 1575-37-7

General procedure: A solution of 10 mmol of the appropriate benzene-1,2-diamine in3.5 mL of acetic acid (AcOH) and 1 mL of water was cooled to 0-5 C,followed by the addition of 15 mmol of sodium nitrite in 2 mL ofwater. The mixture was stirred for 2 h at room temperature. Afterthe completion of the reaction, a solventwas evaporated and the residuewasco-evaporatedwith toluene (3 ¡Á 20mL). The crude productwas partitioned between water (20 mL) and ethyl acetate (20 mL),the organic phase was washed with the saturated solution of sodiumhydrogen carbonate and dried overmagnesiumsulfate (MgSO4). Theproducts were purified by crystallization from nitromethane and/orby column chromatography on silica gel using a chloroform – methanol97:3-95:5 v/v mixture as eluent. Reaction products were analyzedby use of mass-spectrometry (Waters Q-TOF Premier MassSpectrometer) and NMR spectroscopy (Varian INOVA 500 Spectrometer,see Supp. Fig. 1). Purity of the products was assessed using internalstandard quantitative NMR method (qNMR) [49]. It shouldbe noted that the formal qNMR-derived purity determined for 4-BrBt, 4-ClBt, 5,6-Cl2Bt and 5,6-Br2Bt increased significantly upon additiona small amount of water to the DMSO solution, which increasedproton exchange rates. This observation indicates that thenuclear relaxation process accompanying protomeric equilibrium(generally N1-H and N3-H forms predominates) significantly contributeto the obtained NMR spectra, the best proof of which is thestrong broadening of the H-7 resonance line in 4-BrBt and 4-ClBt(Supp. Fig. 1A,B).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1575-37-7, its application will become more common.

Reference:
Article; Szymaniec-Rutkowska, Anna; Bugajska, Ewa; Kasperowicz, S?awomir; Mieczkowska, Kinga; Maciejewska, Agnieszka M.; Pozna?ski, Jaros?aw; Journal of Molecular Liquids; vol. 293; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

A common compound: 111721-75-6, name is 2-Bromo-3-fluoroaniline, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 111721-75-6

To a stirred solution of compound Xlla (155 g, 1.15 mmol) in dichloromethane (2 L) at 0 C under nitrogen atmosphere were added pyridine (750 mL, 5 vol) and 2-bromo-3-fluroaniline (218.0 g, 1.15 mmol). The resulting mixture was continued to stir at room temperature for 16 hours. After that the reaction mixture was quenched with water extracted with dichloromethane (2 x 5 L). The combined organic phase was washed with 1.5N HCl solution (2 x 3 L), brine (1 x 2 L), dried over Na2S04 and concentrated in vacuo. The obtained crude product was purified by column chromatography using silica gel (60-120 mesh) eluting with 20% of ethyl acetate in petroleum ether to get compound Xllb. Yield: 240 g, 64.67% (over a two steps); LC-MS Calc. for CnHnBrFN02, 288.12; Obs: 290.0 [M++2H]; NMR (300 MHz, DMSO-d6): delta 9.26 (s, 1H), 7.61-7.59 (d, 1H, J=8.19 Hz), 7.54-7.49 (m,lH), 7.41-7.34 (m, 1H), 7.17- 7.11 (m, 1H), 5.79-5.75 (d, 1H, J=12.33 Hz), 3.97-3.95 (m, 2H), 1.30-1.25 (m, 3H).

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, 111721-75-6, other downstream synthetic routes, hurry up and to see.

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

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

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

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