Category: bromides-buliding-blocks

Electric Literature of 117635-21-9,Some common heterocyclic compound, 117635-21-9, name is 1,4-Dibromo-2,5-dihexylbenzene, molecular formula is C18H28Br2, 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.

Step 3: In the dry box the mixture of boronic acid pinacol ester,3, (5.8g.16.B2mmol), 1,4-dlbmmo-295-dthexylbenzene(3.4g, 8.4mmol), .Aiiquat 336(0.Bg), and Pd(PP%)4 (0.486g, 0421 mmol) in degassed toluene (lOOmL) was prepared. Outside dry box, the degassed Na2003 (2.87g, 2523mmo1 In 50 mL of water) solution was added to the fomier mixture under nitrogen, and then the resultant mixture was stirred at 90C for 42hrs. Theorganic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined orgqnlc layers were dried over anhydrous MgSO4. Filtration, concentration & the filtrate, and then the silica column chromatography (0-3% ethyl acetae in hexane) provided the desired product (2Mg, 8% yield) as a viscous liquid

The synthetic route of 117635-21-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; RADU, Nora Sabina; FENNIMORE, Adam; WO2015/89027; (2015); A1;,
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Reference of 174508-31-7, A common heterocyclic compound, 174508-31-7, name is 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine, molecular formula is C6H4Br2O2S, 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 5,7-dibromo-2,3-dihydrothieno[3,4-b]-1,4-dioxin were added 2.0 equivalents of tert-butyl 4-tributyltin-2,3-dihydro-2-oxo-1H-thieno[3,4-d]imidazole-1-carboxylate obtained in the same manner as described in Example 7, dry 1,4-dioxane in an amount equivalent to 10 ml/mol relative to 5,7-dibromo-2,3-dihydrothieno[3,4-b]-1,4-dioxin, and 0.1 equivalents of trans-dichlorobistriphenylphosphine palladium. Under argon gas atmosphere, a reaction was advanced by refluxing at 120 C. for 40 hours, and then the reaction was stopped by adding an excessive amount of a saturated aqueous ammonium chloride solution. The resulting reaction liquid was filtered while being diluted with ethyl acetate, and to the resulting filtrate was added three-fold volume of a saturated aqueous potassium fluoride solution, followed by stirring for 2 hours. After the removal of the aqueous phase and insoluble matter, the organic layer containing the product was dried over sodium sulfate, then the solvent was distilled off, and the residue was purified by silica gel column chromatography using an ethyl acetate/hexane solvent, so that tert-butyl 4-[7-(2,3-dihydro-2-oxo-1-tert-butoxycarbonyl-1H-thieno[3,4-d]imidazol-4-yl)-2,3-dihydrothieno[3,4-b]-1,4-dioxin-5-yl]-2,3-dihydro-2-oxo-1H-thieno[3,4-d]imidazole-1-carboxylate was obtained.

The synthetic route of 174508-31-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kuraray Co., Ltd.; Kondou, Yoshirou; Nakano, Kirihiro; Otake, Tomiaki; US8519150; (2013); B2;,
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Application of 583-70-0,Some common heterocyclic compound, 583-70-0, name is 2,4-Dimethylbromobenzene, molecular formula is C8H9Br, 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.

Add 2,4-dimethylbromobenzene to a 500 mL three-necked flask equipped with magnetic stirring at room temperature.2,4-Dimethylaniline, Pd2(dba)3, tri-tert-butylphosphine, sodium t-butoxide, toluene.After the addition, the nitrogen gas was replaced 3 times, the stirring was started, and the oil bath was heated and heated to reflux for 5 hours.The TLC tracking reaction showed that the two starting materials were completely reacted (PE/EA = 20:1, product Rf = 0.8) and the reaction was stopped. The reaction solution was cooled to room temperature, stirred for 10 minutes with pure water, separated, and the aqueous phase was extracted with toluene, and the toluene phase was combined and saturated.Washed with brine, dried over anhydrous sodium sulfate, filtered and evaporatedDilute the crude product with as little petroleum ether as possible: dichloromethane = 10:1, and place the liquid on a silica gel column.Keep the polarity of the eluent unchanged with petroleum ether: dichloromethane = 10:1 until the product is rinsed.Dry under reduced pressure to give an off-white solid.Recrystallization from n-hexane gave 13 g of a white crystalline solid.HPLC 99.18%, yield 57%.

The synthetic route of 583-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Gu’an Dingcai Technology Co., Ltd.; Gao Wenzheng; Ren Xueyan; (34 pag.)CN109665935; (2019); A;,
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Application of 314084-61-2, A common heterocyclic compound, 314084-61-2, name is 2-Bromo-1,3-diethyl-5-methylbenzene, molecular formula is C11H15Br, 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.

Dihydro-1H-pyrazolo[1,2-d][1,4,5]oxadiazepine-7,9(2H,8H)-dione (3.4 g, 20 mmol) at 20 C Soluble in 40mL dimethylformamide,And added 2,6-diethyl-4-methylbromobenzene (4.09 g, 18 mmol) andPd(PPh3)2Cl2 (1.26 g, 1.8 mmol) was then stirred at 135 C for 6 hours. After cooling the above reaction system to room temperature, 200 mL of ethyl acetate and 200 mL of diethyl ether were added, and the reaction mixture was poured into a suction filter.100 mL of water and 100 mL of dichloromethane were added to the filtered residue.Acidified with hydrochloric acid. The organic phase was separated, dried and concentrated by evaporation.The residue was chromatographed on silica gel column (ethyl acetate / petroleum ether = 2:1 (V/V))8-(2,6-Diethyl-4-methylphenyl)tetrahydropyrazolo[1,2-d][1,4,5]oxazepine-7,9(2H,8H) -dione4.72 g, yield 82.9%.

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; Lanzhou Fine Chemical High Technology Development Corporation; Gansu Chemical Institute Co., Ltd.; Liu Rong; Wang Xiaoxia; Ji Pengyan; Wei Wanlei; He Kaiyu; Liu Yunli; (9 pag.)CN108864144; (2018); A;,
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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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Bromo-5-(trifluoromethyl)aniline

To a mixture of 3-amino-5-bromobenzotrifluoride (1.0 g, 4.17 mmol) in pyridine (10 mL) at 0- 5C was added dropwise methanesulfonyl chloride (0.389 mL, 5 mmol). The reaction mixture was stirred at rt for 4 days. As the reaction was not completed, the reaction mixture was then heated in a microwave oven at 150C for 15 min. There was no evolution, so the reaction was stopped. The reaction mixture was concentrated until dryness, and the residue was co- evaporated with toluene. The residue was then diluted with a saturated aqueous solution of NaHC03 and extracted with DCM. The organic layer was dried over MgS04 and evaporated. Purification by Flash chromatography using CombiFlash Companion ISCO system (Redisep silica 12g column, eluting with Cyclohexane/EtOAc 100:0 to 70:30) gave the title compound (1.05 g, 79% yield) as a white solid. 1H-NMR (400 MHz, DMSO-d6, 298 K): ? ppm 3.14 (s, 3H) 7.48 (s, 11-1) 7.64 (s, 11-1) 7.68 (s, 1 H) 10.42 (s, 1 H). MS(10): 316.3-318.2 [M-1]

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 54962-75-3.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; LEWIS, Ian; SMITH, Alexander, Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; WOLF, Romain; ZECRI, Frederic; WO2013/57711; (2013); A1;,
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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. 348-57-2, name is 1-Bromo-2,4-difluorobenzene, A new synthetic method of this compound is introduced below., name: 1-Bromo-2,4-difluorobenzene

Preparation 131 ,5-dibromo-2,4-difluorobenzeneTo a solution of l-bromo-2,4-difluorobenzene (19.3 mL, 171 mmol) in CH2CI2 (100 mL) was added iron (3.15 g,56 mmol). To this stirred suspension was added a solution of bromine (1 1 mL, 214 mmol) in CH2CI2 (25 mL) drop wise over 30 min. The resulting mixture was stirred at rt overnight. The reaction mixture was slowly poured into saturated aqueous Na2S203 (200 mL), and the resulting mixture was stirred at rt for 30 min. This was extracted with CH2C12 (3 x 80 mL). The combined extracts were washed with brine, dried over MgS04, filtered and concentrated in vacuo to give 1,5-dibromo- 2,4-difluorobenzene (40 g, 86 % yield) as a brown oil. XH NMR (500 MHz,CHLOROFORM-d) delta 7.79 (t, J=7.0 Hz, 1H), 7.00 (t, J=8.2 Hz, 1H).

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; BRISTOL-MYERS SQUIBB COMPANY; WU, Yong-Jin; WO2012/162334; (2012); A1;,
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Application of 626-88-0,Some common heterocyclic compound, 626-88-0, name is 1-Bromo-4-methylpentane, molecular formula is C6H13Br, 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: A solution of secondary amine (0.55 mmol), the appropriate alkyl bromide (0.36-0.46 mmol) and triethylamine (0.55 mmol) in N,N-dimethylformamide (3 mL) was stirred for 18 h at room temperature. The solvent was evaporated under reduced pressure and concentrated sodium carbonate solution (30 mL) was added to the crude residue. The aqueous solution was extracted with CH2Cl2 (3?30 mL), the combined organic layers were dried over MgSO4 and evaporated. The crude material was purified by flash column chromatography (CH2Cl2:CH3OH, 9:1 and 1% NEt3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-methylpentane, its application will become more common.

Reference:
Article; Keller, Marco; Wolfgardt, Annette; Mueller, Christoph; Wilcken, Rainer; Boeckler, Frank M.; Oliaro-Bosso, Simonetta; Ferrante, Terenzio; Balliano, Gianni; Bracher, Franz; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 13 – 22;,
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Synthetic Route of 615-54-3, The chemical industry reduces the impact on the environment during synthesis 615-54-3, name is 1,2,4-Tribromobenzene, I believe this compound will play a more active role in future production and life.

Step 1: Into a 100-nt 3-necked round-bottom flask, was placed a mixture of 1,2.4- tribromobenzene (5,20 g, 16.52 mmol, 1.00 equiv) and 2-methylfuran (4.18 g. 50.91 mmol,3.00 equiv) in toluene (30 mL) with stirring at -30 C, followed by the drop-wise addition of n-BuLi (7.48 mL, 1.10 equiv). The resulting mixture was stirred for 30 mm at -30 C then it was quenched by the addition of 50 mL of 1120, cooled to RT and extracted with 3 x 50 mL of ethyl acetate. The organic layer was washed with 200 mL of 1120, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gelcolumn chromatography eluting with ethyl acetate/petroleum ether (1:3) to deliver 2.10 g (54%) of a mixture of (+)-4-bromo- i-methyl-li -oxatricyclo [6.2.1. 02?7jundeca-2,4,6,9- tetraene and (+)-5-bromo- i-methyl-il -oxatricyclo[6. 2.1.0271 undeca-2,4,6,9-tetraene as a light yellow solid. Step 2: Into a l00-mL 3-necked round-bottom flask, was placed a solution of (+)-4- bromo- 1-methyl-il -oxatricyclo [6.2.1.0271 undeca-2,4,6,9-tetraene and (+)-5-bromo- 1-methyl- l1-oxatricyclo[6.2.1.02?7jundeca-2,4,6,9-tetraene (2.10 g, 8.86 mmol, 1.00 equiv) in chloroform (30 mL) with stirring at rt, followed by the slow addition of a solution ofbis(pyridin-2-yl)-1,2,4,5-tetrazine (2.40 g, 10.16 mmol, 1.10 equiv) in chloroform (20 mL). The resulting mixture was stirred for 1 h at 50 C to deliver the mixture of corresponding isobenzofurans intermediate (50 mL) as a red solution. To this solution into a 100-mL 3- necked round-bottom flask at 0 C was added a solution of [5-(methoxycarbonyl)-2- (trimethylsilyl)phenyl](phenyl)iodanium trifluoromethanesulfonate (5.60 g, 9.99 mmol, 1.00equiv) in dichioromethane (40 mL), followed by TBAF (5.23 g, 20.00 mmol, 2.00 equiv). The resulting mixture was stirred for 30 mm at 0 C then it was concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:3) to deliver 900 mg (26%) of (+)-methyl 12-bromo-8-methyl-15- oxatetracyclo [6,6,1,027, 4i pentadeca-2(7),3 ,5,9, 11,13 -hexaene-4-carboxylate, (+)-methyl11 -bromo-8-methyl- 1 5-oxatetracyclo[6. 6.1. 02?.O9?14jpentadeca-2(7),3,5,9,1 1,1 3-hexaene-4- carboxylate, (+)-methyl 1 2-bromo- 1-methyl-i 5-oxatetracyclo-[6. 6,i,02?. 09?14jpentadeca- 2(7),3,5,9. 11,1 3-hexaene-4-carboxylate and (+)-methyl ii -bromo- i-methyl-i 5- oxatetracyclo [6.6. i .027. 14j pentadeca-2(7),3 ,5 ,9, ii, i 3 -hexaene-4-carboxylate as a light yellow solid. Step 3: Into a 50-mL round-bottom flask, was placed a mixture of (+)-methyl i2- bromo-8-methyl-1 5-oxatetracyclo[6. 6.1.02,7. 09?4jpentadeca-2(7),3,5,9, ii, i 3-hexaene-4- carboxylate (+)-methyl ii -bromo-8-methyl- i 5-oxatetracyclo[6. 6. i .02,7. ue 14j pentadeca2(7),3,5 ,9. 11,1 3-hexaene-4-carboxylate, (+)-methyl 1 2-bromo- 1-methyl- 15- oxatetracyclo[6.6. 1.027.09141 -pentadeca-2(7),3.5.9,1 1, i 3-hexaene-4-carboxylate and (+)-methyl ii -bromo- i-methyl-i 5-oxatetracyclo[6. 6. i .02,7. 09?4jpentadeca-2(7),3,5,9, ii ,13- hexaene-4-carboxylate (500.0 mg, 1.45 mmol, 1.00 equiv), dioxane/H20 (5/0.5 mL), (4- fluorophenyl)boronic acid (665.0 mg, 4.75 mmol, 1.50 equiv), sodium carbonate (46i.0 mg, 4.35 mmol, 3.00 equiv) and Pd(dppf)Cl2 (53.0 mg, 0.07 mmol, 0.05 equiv) with stirring under N2. The resulting mixture was stirred for 3 h at 90 C then it was cooled to RT andconcentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (iS) to afford 4 i 0.0 mg (79%) of a mixture of (+)-methyl 1 2-(4-fluorophenyl)-8-methyl- i 5-oxatetracyclo- [6.6. i .02,7. ?4jpentadeca- 2(7),3,5 ,9. ii, 1 3-hexaene-4-carboxylate, (+)-methyl ii -(4-fluorophenyl)-8-methyl- 15-oxatetracyclo [6.6.1.02,7. ue 14j pentadeca-2(7),3 ,5,9, 11,13 -hexaene-4-carboxylate, (+)-methyl 12-(4-fluorophenyl)-1 -methyl-i 5-oxatetracyclo[6. 6.1. 02?7.09?4j-pentadeca-2(7),3,5,9, 11,13- hexaene-4-carboxylate and (+)-methyl ii -(4-fluorophenyl)- 1-methyl-i 5- oxatetracyclo [6.6.1.027. 14j pentadeca-2(7),3 ,5 ,9, 11,13 -hexaene-4-carboxylate as a lightyellow solid..

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, 1,2,4-Tribromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; LI, Zhe; ZANCANELLA, Manuel; YU, Chul; SETTI, Lina; SHAM, Hing; XU, Qing; YEE, Calvin; YU, Ming; (402 pag.)WO2016/201052; (2016); A1;,
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Related Products of 142808-15-9, 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. 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00199] step 2: (R)-tert-butyl 2-(3 -fluoro-4-(trifluoromethyl)benzoyl)pyrrolidine- 1 -carboxylate. To a stirred solution of 4-bromo-2-fluoro-l-(trifluoromethyl)benzene (4.854 g, 19.98 mmol) and ether (50 mL) cooled to -78 C under nitrogen was added w-butyl lithium (7.99 mL, 19.98 mmol) slowly over 10 min. The reaction was transferred via cannula to a solution of 42b (4.30 g, 16.65 mmol) in THF (50 mL) cooled to -78 C. The reaction was stirred for 10 min after all aryl lithium was added. The reaction was quenched with water and extracted with DCM. The organic layer was dried (MgS04), concentrated and the crude product purified by Si02 chromatography eluting with an EtOAc/hexane gradient (1 to 5% EtOAc). A close running impurity was not removed by this purification. The compound was further purified on a SP4 reverse phase column chromatography eluting with MeCN/water gradient (65 to 100% MeCN) to afford 2.105 g (33.2%) of 44.

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

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; BLAKE, James, F.; CHEN, Huifen; CHICARELLI, Mark, Joseph; DEMEESE, Jason; GARREY, Rustam, Ferdinand; GAUDINO, John; GAZZARD, Lewis; KAUS, Robert J.; KINTZ, Samuel; MOHR, Peter J.; MORENO, David, A.; SCHWARZ, Jacob; SIEDEM, Christopher, S.; WALLACE, Eli, M.; WO2013/20062; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 3814-30-0, These common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, 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.

A solution of diethyl malonate (36.91 g, 230.4 mmol), anhydrous methanol (400 mL), and NaOMe (25% in methanol, 49.79 g, 230.4 mmol) is stirred at reflux for one hour under nitrogen. Bromomethyl-cyclopentane (31.31 g, 192.0 mmol) is added to the mixture, and stirred for an additional 3 hours. A solution of NaOH (23.04 g, 576.0 mmol) in water (400 mL) is added, and the mixture is stirred for an additional 1 hour at reflux. The mixture is cooled, diluted with water, and extracted with ether. The ether layer is discarded, and the aqueous layer is acidified with 1N HCI to pH=1. The aqueous layer is extracted with EtOAc. The EtOAc layers are combined, dried over Na2SO4, and concentrated. This gives 2- cyclopentylmethyl-malonic acid (21.0 g, 59% yield) as a white solid.

Statistics shows that (Bromomethyl)cyclopentane is playing an increasingly important role. we look forward to future research findings about 3814-30-0.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; VICURON PHARMACEUTICALS, INC; WO2006/127576; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary