Category: bromides-buliding-blocks

Synthetic Route of 955959-84-9,Some common heterocyclic compound, 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, molecular formula is C18H11BrO, 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.

0.21 g of palladium(II) acetate, xylene (20 mL), and 0.76 g of tri-tert-butylphosphine were added.Stirred at 60 °C for 30 minutes. The above solution was added to a flask heated to 60°C under nitrogen to give the above compound 4 (16,18-Dihydrobenzo[4,5]furo[3,2-a]benzofurano[2′,3′:6,7]indolo[3,2-h]carbazole 7.4 g), 4-(4-bromophenyl)dibenzo[b,d]furan (13.2 g) and sodium tert-butoxide 5.2 g (54 mmol) were added to the above solution together with xylene (180 mL). Then, it heated up at 130 °C , and it heat-stirred for 6 hours. After cooling to room temperature, 200 mL of water was added. After the organic layer was extracted with chloroform, the organic layer was dried over MgSO4 , the solvent was removed, and silica gel column chromatography was performed, whereby Compound A-10 (6.4 g, 41percent) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Bromophenyl)dibenzo[b,d]furan, its application will become more common.

Reference:
Patent; Co., Ltd. LG Chemical; Hong Wanshao; He Zaicheng; Xu Shangde; Jin Zhengfan; Li Zaizhuo; Jin Yuanhuan; (73 pag.)CN108017654; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

17247-58-4, name is (Bromomethyl)cyclobutane, 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. Safety of (Bromomethyl)cyclobutane

[4~NitiO-3-(2,2,2~trifluoro-ethoxy)-phenyl]-a.cetic acid methyl ester (33 g, 94.5 mmol) and (bromomethyl)cyclobutane (17 g, 1 14.1 mmol) were mixed in DMSO (50 mL) and KOH (6.4 g, 14,1 mmol) was added in portions over 15 min. The reaction mixture was stirred for 16 h and water (100 mL) was added. The reaction mixture was extracted with EtOAc (3 x 50 mL). The combined organic phases were dried over MgS04and evaporated to give a crude yellow oil, which was purified by silica gel gradient column chromatography using Heptane-EtOAc (9: 1 – 4: 1) to give 15 g (40%) of the product as a. yellow oil. (The synthesis was repeated with temperature kept at 40 C over 16 h to give the product in quantitative yield).JH NMR (300 MHz, CDC /TMS): delta 7.86 (d, ./ 8.0 Hz, IH), 7.12-7.09 (m, 2H), 4.50 (q, J – 7.7 Hz, 2H), 3.68 (s, 3H), 3.55 (t, J = 7.3 Hz, I H ). 2.22,-2.10 (m, 2H), 2.03-1.75 (m, 5H), 1.70-1.55 (m, 2H).13C NMR (75 MHz, CDC TMS): 5 172.9, 150.5, 146.4, 139.4, 126.0, 122.7, 122.6 (d, VCF= 277.6 Hz), 1 16.0, 67.5 (q,CF36.7 Hz), 52.3, 49.6, 40.7, 33.9, 28.2, 27.9, 18.4.

The synthetic route of 17247-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; KOENIG, Gerhard; BLAIN, Jean-francois; WO2013/106328; (2013); 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. 4549-33-1, name is 1,9-Dibromononane, A new synthetic method of this compound is introduced below., Computed Properties of C9H18Br2

Example 25 (n=9); (a) 1, 1′- [ (Nonane-l,-9-diyl) dioxylbis [ (11S, llaS)-10- (tert- butyloxycarbonyl)-7-methoxy-11-(tetrahydro-pyran-2-yloxy)-2- methylidene-1, 2, 3, 10, 11, 11a-hexahydro-5H-pyrrolo [2, 1- c] f, 4Jbenzodiazepine-5-one] (28b); 1,9-Dibromononane (35.75 mg, 0.125 mmol, 0.5 equiv. ) was added to the mixture of monomer 27 (115 mg, 0.25 mmol, 1.0 equiv. ), potassium carbonate (53 mg, 0.50 mmol, 2.0 equiv. ) and a catalytic amount of potassium iodide (1 mg) in dry DMF (30 mL), and the resulting mixture was heated to 90 C under a nitrogen atmosphere for 5 h. Removal of excess solvent under reduced pressure afforded a crude solid, which was subjected to flash column chromatography (Si02, 50% EtOAc-hexane) to afford the dimerized compound 28b (89 mg, 0.085 mmol, 68% yield, mixture of diastereomers from THP protecting group) as a solid: [alpha]29D = +36 (c = 0. 11, CHCl3) ; 1H NMR (CDC13, 400 MHz): No. 1.25-1. 67 (m, 72H, 14-H, 15-H, 16-H, Boc, THP), 1.70-1. 91 (m, 16H, 13-H, THP), 2. 51-2.58 (m, 2H, 1-H), 2.72-2. 81 (m, 2H, 1-H), 2.84-2. 97 (m, 4H, 1-H), 3.51-3. 65 (m, 8H, lla-H, THP), 3. 85-4. 19 (m, 28H, 3-H, 12-H, 7-OMe, THP), 4.26-4. 38 (m, 4H, 3-H), 5.00-5. 18 (m, 12H, 2a-H, THP), 5.65-5. 74 (d, 2H, 11-H), 5.76-5. 88 (d, 2H, 11-H), 6.49 (s, 2H, 9-H), 6.85 (s, 2H, 9-H), 7.16 (s, 2H, 6-H), 7.19 (s, 2H, 6-H) ; 13C NMR (CDCl3, 100 MHz) : No. 20.2, 25.2, 25.9, 28.1, 28.2, 29.0, 29.3, 29.4, 31.0, 31. 1,35. 1,35. 4, 50.6, 56.1, 59.9, 60.0, 63.5, 68.9, 69.2, 91.1, 96.2, 100.3, 109.3, 110.4, 110.5, 114.8, 114. 9,129. 8,142. 1,148. 6,148. 9, 167.2 ; IR (neat): 2935,2856, 1704,1645, 1604,1511, 1454,1430, 1401,1367, 1325,1255, 1210,1163, 1119, 1020,907, 729 cm~1 ; MS (ES+) m/z (relative intensity) 1068 ([M + Na]+., 13), 1045 ( [M + H]+., 100), 1046 ([M + 2H] +-, 65), 943 (42), 843 (28).

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; SPIROGEN LIMITED; WO2005/85259; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 59907-13-0, These common heterocyclic compound, 59907-13-0, name is 2-Bromo-1-fluoro-3-methylbenzene, 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 solution of 2-bromo-l-fluoro-3-methylbenzene (2.5 g, 10 mmol) in THF (20 mL) at -70 C was added n-BuLi (1.6 M in hexane) (6.9 mL, l l .Ommol) dropwise over 5 min by syringe along the wall of the flask. After adding, the reaction was stirred at this temperature for 30 min. Then the resulting solution was added into a solution of (S)- tert-butyl l,6-dioxohexahydropyrrolo[l,2-a]pyrazine-2(lH)-carboxylate (2.07 g, 11.0 mmol) in THF (10 mL). After stirred at -70C for 5 min, the reaction mixture was quenched with saturated NH4CI and extracted with EtOAc (2 x 20 mL), washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to give the title compound (2.2 g, yield : 40%); m/z (ES+) : 365 [M + H] + .

Statistics shows that 2-Bromo-1-fluoro-3-methylbenzene is playing an increasingly important role. we look forward to future research findings about 59907-13-0.

Reference:
Patent; LEO PHARMA A/S; BLADH, Haakon; FELDING, Jakob; ZHOU, Ding; CAI, Zhen-wei; SØRENSEN, Morten Dahl; WO2015/24878; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 955959-84-9, 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.

In an argon atmosphere, in a three-necked 100mL flask, compound (x) 0.8g, the compound (xi) 0.54g, bis(dibenzylideneacetone)palladium (0) (Pd(dba)2) 0.06g, tri-t-butylphosphine ((t-Bu)3P) 0.12g, was added to sodium t-butoxide 0.3g, was heated under reflux for 7 hours in 30mL of toluene solvent. After air-cooling, water was added The organic layer was separated, and the solvent was distilled off. The crude product thus obtained was purified by silica gel column chromatography (dichloro methane and using a mixed solvent of hexane) was subjected to recrystallization with toluene and hexane mixture solvent to give the compound A-35 as a white solid 0.95g (80percent yield)

The synthetic route of 4-(4-Bromophenyl)dibenzo[b,d]furan has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung DisplayCo., Ltd.; Huchiwaki, Junta; Oyama, Hiromi; Miyata, Yasuo; Sakamoto, Naoya; Ueno, Masatsuku; Takada, Echinori; (155 pag.)KR2015/90021; (2015); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 454-79-5, name is 2-Bromo-5-(trifluoromethyl)aniline, 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 454-79-5, category: bromides-buliding-blocks

70% Sulfuric acid (18 mL) was added drop-wise to the solution of 2-bromo-5- (trifluoromethyl)aniline (5.0 g, 21.0 mmol, 1.0 eq), propane- 1, 2,3 -triol (3.8 g, 42.0 mmol, 2.0 eq) and sodium m-Nitrobenzene sulfonate (7.3 g, 32.55 mmol, 1.55 eq) at 0 C and the mixture was stirred under nitrogen atmosphere, at 150 C for 4 h. After complete consumption of starting material, the mixture was cooled to ambient temperature, poured into chilled water and filtered through a celite bed. The filtrate was neutralized with 2N aqueous NaOH, which led to a precipitate, which was filtered and dried under vacuum to obtain 8-bromo-5- (trifluoromethyl)quinoline. LCMS: Purity 95.13%. MS calculated for [M] 274.96 and found [M+H] +276.04.

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, 2-Bromo-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; BOWERS, Simeon; BARTA, Thomas E.; BOURNE, Jonathan William; (208 pag.)WO2017/147328; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2924-09-6, 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. 2924-09-6, name is 5-Bromo-2-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In an argon atmosphere, 106 mL of water was added to 10g of 5-bromo-2-fluoroaniline, and the mixture wasstirred, followed by addition of 79.2 mL of concentrated hydrochloric acid. The resulting mixture was cooled in ice, andan aqueous solution of 4.36g of sodium nitrate was added dropwise. While cooling in ice, the resultant was stirred for30 minutes, and then an aqueous solution of 87.3g of potassium iodide was added. After extraction with ethyl acetate,an organic layer was washed with an aqueous solution of a saturated sodium hydrogen carbonate and an aqueoussolution of sodium sulfite and dried with magnesium sulfate. Then, the solvent was distilled off under reduced pressure.Residues were purified by silica gel column chromatography, whereby 11.5g (yield: 73%) of 5-bromo-2-fluoroiodebenzenewas obtained.

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

Reference:
Patent; Idemitsu Kosan Co., Ltd; ITO, Hirokatsu; SAITO, Hiroyuki; MIZUKI, Yumiko; KAWAMURA, Masahiro; EP2924029; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 51376-06-8, 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. 51376-06-8 name is 5-Bromobenzo[c][1,2,5]oxadiazole, 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.

Cesium carbonate (0.46 g), 5-bromo-2,1,3-benzoxadiazole (0.23 g), 2,2′- bis(diphenylphosphino)-1,1′-binapthyl (0.074 g) and tris-(dibenzylideneacetone) dipalladium(O) (0.054 g) were added to a solution of N-{[(5S)-3-(3-fluoro-4-piperazin-1- ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide (0.4 g) (which can be prepared according to Example l(k) in WO 93/23384, at page 14) in dry dimethyl formamide (15 mL) and the reaction mixture was heated at 100 C for 17 hours. The reaction mixture was filtered and the solvent was evaporated. The crude product thus obtained was purified by column chromatography using 2 % methanol in dichloromethane and sonicated in ether to yield the title compound (0.12 g).Melting point: 201-222 C; EIMS (m/z): 455;1HNMR(CDCl3): delta 7.71 (d, 1H), 7.48 (dd, 1H), 7.33 (dd, 1H), 7.12 (dd, 1H), 6.98 (t, 1H), 6.79 (s, 1H), 5.99 (t, 1H), 4.76 (m, 1H), 4.02 (t, 1H), 3.85-3.55 (m, 3H), 3.47 (m, 4H), 3.24 (m, 4H), 2.03 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromobenzo[c][1,2,5]oxadiazole, and friends who are interested can also refer to it.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2006/35283; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2862-39-7,Some common heterocyclic compound, 2862-39-7, name is 2-Bromo-N,N-dimethylethanamine hydrobromide, molecular formula is C4H11Br2N, 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: To the suspension of compound 11a-11e or 13 (1.5 mmol) inDCM (3 mL) was added TFA (3 mL). The mixturewas stirred at roomtemperature for 2 h and was concentrated under vacuum. Theproduct was then dissolved in DMF (6 mL) and added Et3N (1 mL)without further purification. The reaction mixture was stirred for1 h and was added CS2 (0.14 mL, 2.25 mmol) to continuously stir for 30 min. A series of different of halogen or alkene substitutedcompounds (1.5 mmol) were added respectively and the mixturewas stirred at 50 C overnight. The mixture was cooled to roomtemperature and extracted with dichloromethane (20 mL x 3). Theorganic phase was washed with brine (15mL x 3), dried overanhydrous Na2SO4 and concentrated under vacuum. The residuewas purified by column chromatography to provide the target products.

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

Reference:
Article; Su, Yue; Li, Ridong; Ning, Xianling; Lin, Zhiqiang; Zhao, Xuyang; Zhou, Juntuo; Liu, Jia; Jin, Yan; Yin, Yuxin; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 32 – 46;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 583-75-5, 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 583-75-5 as follows.

In a 2000 ml beaker to 400 ml of 23percent aqueous HBr, 46.5 g (0.25 mol) of melted 2-methyl-4-bromoaniline was slowly added. This mixture was stirred for 20 minutes using a mechanical stirrer, cooled to -50C. Then a solution of 22.4 g (0.33 mol) Of NaNO2 in 130 ml of water was added dropwise for 1 hour at this temperature. The diazonium reagent obtained was added in several portions to a solution of 35.9 g (0.25 mmol) of CuBr in 100 ml of 47percent HBr at O0C. The resulting mixture was warmed to 7O0C, stirred for 30 minutes at this temperature, and then cooled to room temperature. The product was extracted with 3 x 200 ml of methyl-tert-butyl ether. The combined extract was dried over K2CO3 and evaporated to dryness. The crude product was purified by first using a short Silica Gel 60 column (40-63 mum, d 60 mm, 1 40 mm; eluent: hexanes). Fractional distillation gave colorless oil, b.p. 100-102°C/10 mm Hg. Yield 36.1 g (58percent). Anal. calc. for C7H6Br2: C, 33.64; H, 2.42. Found: C, 33.79; H, 2.50. 1H NMR (CDCl3): delta 7.39 (m, IH, 5-H), 7.37 (m, IH, 3-H), 7.18 (m, IH, 6- H), 2.38 (s, 3H, Me).13C NMR (CDCl3): delta 139.9, 133.6, 133.5, 130.3, 123.5, 120.9, 22.7.

According to the analysis of related databases, 583-75-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXXONMOBIL CHEMICAL PATENTS INC.; WO2007/70041; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary