Category: bromides-buliding-blocks

Synthetic Route of 1435-51-4, These common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, 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.

l,3-Dibromo-5-fluorobenzene (10.2 g, 40.7 mmol) was dissolved in 1,4- dioxane. Pyridine-4-ylboronic acid (5 g, 40.7 mmol), tetrakis(triphenylphosphine)- palladium(O) (462 mg, 0.41 mmol), and K2CO3 (11.22 g, 81 mmol) were added, and the mixture was heated at 900C for 4 h. The reaction was diluted with EtOAc, washed with aq. NaHCO3 and dried and removed. Purification via column chromatography afforded 4-(3-bromo-5-fluorophenyl)pyridine (6 g, 59%). 1H NMR (400 MHz, CDCl3): delta 8.73 (d, IH), 8.58 (d, IH), 7.77 (dd, IH), 7.45 (s, IH), 7.34-7.31 (m, IH), 7.22 (t, IH), 7.18- 7.15 (m, IH).

Statistics shows that 1,3-Dibromo-5-fluorobenzene is playing an increasingly important role. we look forward to future research findings about 1435-51-4.

Reference:
Patent; SEPRACOR INC.; BURDI, Douglas; SPEAR, Kerry, L.; HARDY, Larry, Wendell; WO2010/114971; (2010); A1;,
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Related Products of 7051-34-5,Some common heterocyclic compound, 7051-34-5, name is (Bromomethyl)cyclopropane, molecular formula is C4H7Br, 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.

4-Hydroxybenzaldehyde (3.00 g, 0.0246 mol), bromomethylcyclopropane (3.58 ml, 0.0369 mol) and K2CO3 (6.8 g, 0.050 mol) were taken in acetone (80 ml) and refluxed for 24 h. The reaction mixture was cooled to room temperature, the insolubles filtered through Celite and the solvent was evaporated to obtain a crude residue. Purification of the residue by column chromatography (silica gel 60-120 mesh, EtOAc:Hexane 0.5:9.5) afforded 3.6 g (83.14%) of 4-cyclopropylmethoxybenzaldehyde. LCMS [M+H]+ 177.0 IH-NMR (CDCl3): 9.877 (s, IH), 7.813-7.833 (d, 2H, J=8 Hz), 6.984-7.004 (d, 2H, J=8 Hz), 3.882-3.899 (d, 2H, J= 6.8 Hz), 1.259-1.295 (m, IH), 0.669-.687 (m, 2H), 0.383 (bs, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Bromomethyl)cyclopropane, its application will become more common.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; SARMA, Pakala, Kumara Savithru; ACHARYA, Vinod, Parameshwaran; KASIBHATLA, Srinivas, Rao; VISWANADHAN, Vellarkad, Narayana; SHEKHAR, Polisetti; BISCHOFF, Alexander; WO2010/127212; (2010); 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. 3814-30-0, name is (Bromomethyl)cyclopentane, A new synthetic method of this compound is introduced below., Computed Properties of C6H11Br

Preparation 78 6-Bromo-1-(cyclopentylmethyl)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine Sodium hydride (60% in mineral oil, 10.8 mg, 0.271 mmol) was added to a solution of 6-bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 50 mg, 0.180 mmol) in DMF (780 mL). The reaction mixture was then stirred for 15 minutes at room temperature before the addition of (bromomethyl)cyclopentane (44 mg, 0.271 mmol). The reaction mixture was then stirred overnight at room temperature and for 24 hours at 60 C. Sodium hydride (60% in mineral oil, 5 mg, 0.125 mmol) was added and the reaction was stirred for another 7 hours at 60 C. The reaction mixture was then diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude was purified via Biotage silica gel column chromatography eluting with (DCM/EtOAc 99/1 to 80/20) to afford the title product as a colourless oil (45 mg, 69%). 1H NMR (500 MHz, CDCl3) d 1.10-1.19 (m, 2H), 1.46-1.64 (m, 6H), 2.24-2.33 (m, 1H), 4.03 (s, 3H), 4.09 (d, J=7.6 Hz, 2H), 6.53 (d, J=0.9 Hz, 1H), 7.45 (t, J=0.9 Hz, 1H), 7.59 (s, 1H), 7.68 (s, 1H), 8.60 (d, J=0.9 Hz, 1H). LC (Method B)-MS (ESI, m/z) tR 3.03 min, 359 [(M+H+), 100%].

The synthetic route of 3814-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; Bavetsias, Vassilios; Atrash, Butrus; Naud, Sebastien Gaston Andre; Sheldrake, Peter William; Blagg, Julian; US2013/345181; (2013); A1;,
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Synthetic Route of 40161-54-4, These common heterocyclic compound, 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, 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.

(1) 1-[2-Fluoro-4-(trifluoromethyl)phenyl]butan-1-one To a solution of 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (0.30mL, 2.1mmol) in THF (6mL) was added dropwise 1.5M butyllithium in THF (1.65 mL) at -78C. The mixture was stirred at -78C for 15 minutes, to which was added a solution of butyraldehyde (0.18 mL, 2.5 mmol) in THF (2 ml) at -78C. After stirring at -78C for 30 minutes, the mixture was treated with acetic acid (1 mL)/THF (2 mL), and then followed by water at room temperature. The organic layer was separated, and the aqueous layer was extracted with ether. The combined organic layers were washed with saturated brine. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure to give 1-[2-fluoro-4-(trifluoromethyl)-phenyl]butanol.

Statistics shows that 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene is playing an increasingly important role. we look forward to future research findings about 40161-54-4.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; EP2277874; (2011); 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. 944718-31-4, name is 5-Bromo-1-methyl-1H-benzo[d][1,2,3]triazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-1-methyl-1H-benzo[d][1,2,3]triazole

Methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-7H-benzo[i/][l,2,3]triazoleTo a solution of 5-bromo-l-methyl-iH-benzo[Patent; BIOENERGENIX; MCCALL, John M.; ROMERO, Donna L.; KELLY, Robert C.; WO2012/119046; (2012); A2;,
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Reference of 6274-57-3, 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 6274-57-3 as follows.

a.; A solution of (4-bromobenzyl)dimethylarnine (120 g, 0.50 mole) in THF (2 L) was cooled to -78 0C and treated dropwise with n-BuLi (47 g, 0.728 mole). The reaction mixture was stirred for 1 hour and then butyl borate (194 g, 0.84 mole) was added dropwise. The reaction mixture was stirred for 1 hour, allowed to warm to 0 0C, and then quenched by the addition of water (1.5 L). The reaction mixture was washed with ether (2 x 1 L), and the aqueous layer taken on to the next step.

According to the analysis of related databases, 6274-57-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/18941; (2007); A2;,
Bromide – Wikipedia,
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Application of 138526-69-9, 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. 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a 3000 L reactor, 201.6 kg of KOH was added,Pumped 253.2 kg of 3,4,5-trifluorobromobenzene and 1500 L of methanol,Close the reaction kettle, stirring up to 60 ,After 6 hours of reaction,Raw materials have been basically complete.The material into the crystallization pot with nitrogen into the pot,Stirring and cooling to -5 C,Insulation 5h filter,To give 2,3-difluoro-5-bromoanisole,Yield 92.0%Content of 99.2%. The methanol recovery in the filtrate can be reused.

The synthetic route of 1-Bromo-3,4,5-trifluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Linjiang Chemical Industry Co., Ltd.; Yi, Miao; Yin, Xin; Chen, Huanjun; Wang, Qijin; Xu, Xin; (8 pag.)CN106478377; (2017); A;,
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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. 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, A new synthetic method of this compound is introduced below., Computed Properties of C6H2Br2F2

Under a nitrogen atmosphere, in an 100 ml Schlenk reaction vessel, THF solution 4.5 ml (3.6 mmol) of isopropylmagnesiumbromide (manufactured by Tokyo Chemical Industry Co., Ltd., 0.80M) and THF10ml were added. The mixture was cooled to -75 C,and 2,3-dibromo-thiophene (manufactured by WakoPure Chemical Industries) 873mg (3.61mmol) was added dropwise. after aging at -75 for 30 minutes, diethyl ether solution 3.6ml (3.6mmol) of zinc chloride (Sigma Aldrich, 1.0M) was dropped. After gradually warmed to roomtemperature, the resulting white slurrymixture was concentrated under reduced pressure, to distill off the low-boilingfraction of 10ml. To the resulting white slurry liquid (3 bromothienyl-2-zinc chloride),1,4-dibromo-2,5-difluorobenzene(manufactured by Wako Pure Chemical Industries, Ltd.) 272mg (1.00mmol), tetrakis (tri phenyl phosphine) palladium as catalyst (manufacturedby Tokyo Kasei Kogyo) 39.1mg (0.0338mmol, 3.38 mol% with respect to 1,4 dibromo-2,5-difluorobenzene)and THF10ml were added. After performing reactionfor 8 hours at 60 C, the reaction vessel was water-cooled and by the addition of 3N hydrochloricacid 3ml, reaction was stopped. It was extracted with toluene and the organicphase was washed with brine, and dried with anhydrous sodium sulfate.concentrated under reduced pressure, And the resulting residue was purified bysilica gel column chromatography (from hexane,hexane / dichloromethane = 10/1),further purified by recrystallization from hexane / toluene = 6/4, to give a pale yellow solid 227mg of 1,4-di (3- bromothienyl) -2,5-difluorobenzene(52% yield).

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TOSOH CORPORATION; WATANABE, MAKOTO; (14 pag.)JP5790069; (2015); B2;,
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Related Products of 103-64-0, 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. 103-64-0 name is (2-Bromovinyl)benzene, 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: Typical procedure for the preparation of dimethyl (2-oxo-2-phenylethyl)phosphonate (5a). To a solution of methanol (10 mL), styrene (0.11 g, 1.0 mmol) and dimethylphosphite (0.22 g, 2.0 mmol) was added Mn(OAc)3 (0.54 g, 2.0 mmol) over 30 min at 70 C, and the mixture was stirred for another 30 min to complete the reaction. Then, the solvent was removed under vacuum. To the residue was added water (20 mL) and extracted with ethyl acetate (10 mL*3). The combined organic fractions were dried over anhydrous Na2SO4, and concentrated under vacuum to yield the crude product, which was purified by column chromatography (silica gel, petroleum ether/EtOAc/CH2Cl2(10:1:1)) to give pure dimethyl (2-oxo-2-phenylethyl)phosphonate (5a).

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

Reference:
Article; Zhang, Guo-Yu; Li, Cheng-Kun; Li, Da-Peng; Zeng, Run-Sheng; Shoberu, Adedamola; Zou, Jian-Ping; Tetrahedron; vol. 72; 22; (2016); p. 2972 – 2978;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1435-52-5, These common heterocyclic compound, 1435-52-5, name is 1,4-Dibromo-2-fluorobenzene, 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.

General procedure: 6.16 1-Bromo-4(4′-methoxyphenyl)-2-fluorobenzene (8b): Starting with 6 (100 mg, 0.39 mmol), Cs2CO3 (190 mg, 0.50 mmol), Pd(PPh3)4 (3 molpercent), 4-methoxyphenylboronic acid (59.3 mg, 0.39 mmol) and 1,4-dioxane (4 mL), 8b was isolated as a colorless oil (67 mg, 60percent). 1H NMR (300 MHz, CDCl3): delta = 3.77 (s, 3H, OCH3), 6.90 (td, J = 8.85, 2.18 Hz, 2H, ArH), 7.20-7.27 (m, 3H, ArH), 7.34-7.39 (m, 2H, ArH). 13C NMR (75.46 MHz, CDCl3): delta = 55.3 (OCH3), 114.1 (2CH), 119.6 (d, J = 25.9 Hz, CH), 120.5 (d, J = 9.5 Hz, C), 127.6 (d, J = 3.70 Hz, C), 128.5 (d, J = 12.4 Hz, CH), 129.9 (d, J = 2.8 Hz, CH), 131.4 (d, J = 4.07 Hz, CH), 131.9 (d, J = 2.77 Hz, C), 132.1 (d, J = 9.8 Hz, CH), 159.4 (C), 159.5 (d, JCF = 251 Hz, C). 19F NMR (282.4 MHz, CDCl3): delta = -115.31 (CF). IR (ATR, cm-1): , 2999 (w), 2922 (w), 2835 (w), 2712 (w), 2550 (w), 2158 (w), 2048 (w), 1980 (w), 1891 (w), 1607 (m), 1518 (m), 1477 (s), 1390 (m), 1264 (m), 1247 (s), 1178 (s), 1112 (m), 1037 (m), 963 (w), 869 (s), 807 (s), 719 (m), 636 (w), 570 (m), 539 (s). MS (EI, 70 eV): m/z (percent) = 281 (13) [M]+, 280 (100), 267 (30), 265 (31), 239 (29), 158 (15), 157 (35). HRMS (EI) calcd. for C13H10OBrF [M]+: 281.98731; found 281.98769.

Statistics shows that 1,4-Dibromo-2-fluorobenzene is playing an increasingly important role. we look forward to future research findings about 1435-52-5.

Reference:
Article; Sharif, Muhammad; Maalik, Aneela; Reimann, Sebastian; Feist, Holger; Iqbal, Jamshed; Patonay, Tama?s; Villinger, Alexander; Langer, Peter; Journal of Fluorine Chemistry; vol. 146; (2013); p. 19 – 36;,
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