Month: July 2021

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

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

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

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;,
Bromide – Wikipedia,
bromide – Wiktionary

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

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;,
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. 134168-97-1, name is 3-Bromo-5-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3-Bromo-5-fluoroaniline

To a solution of 3-bromo-5-fluoroaniline (CAS 134168-97-1) (1.0 g, 5.3 mmol) and 2,6-lutidine (2.8 g, 26.5 mmol) in anhydrous DCM (30 mL), was added dropwise 2-chloro-ethanesulfonyl chloride (CAS 1622-32-8) (1.0 g, 6.3 mmol) in DCM (5 mL) at r.t. The mixture was stirred at r.t. for 30 min, and compound 34-A (1.5 g, 16 mmol) was added and stirred for 1 h. Water (50 mL) was added, and the mixture was extracted with EtOAc (100 mL×2). The combined organic layers was washed with sat NaCl (50 mL), dried over Na2SO4, concentrated, and purified by column to give the product (700 mg, yield 37%).

The synthetic route of 134168-97-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chen, Huifen; Crawford, Terry; Harris, Seth F.; Magnuson, Steven R.; Ndubaku, Chudi; Wang, Lan; US2013/324516; (2013); 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. 630-17-1, name is 1-Bromo-2,2-dimethylpropane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-2,2-dimethylpropane

B) 2-methoxy-3-neopentylpyridine Under an argon atmosphere, a solution of 1-bromo-2,2-dimethylpropane (14.8 mL) in diethyl ether (120 mL) was added dropwise to magnesium (3.15 g) at a slow refluxing rate. The reaction mixture was heated under reflux for 30 min, and the obtained solution was added dropwise to a solution of 3-bromo-2-methoxypyridine (4.43 g) and PEPPSI-SIPr (trade name) (805 mg) in THF (80 mL) at room temperature. The reaction mixture was stirred at room temperature for 30 min, and saturated aqueous ammonium chloride solution was added at room temperature. The reaction mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound (4.24 g) as a pale-yellow oil.

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 630-17-1.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIWATASHI, Seiji; SUZUKI, Hideo; OKAWA, Tomohiro; MIYAMOTO, Yasufumi; YAMASAKI, Takeshi; HITOMI, Yuko; HIRATA, Yasuhiro; SHIBUYA, Akito; EP2816023; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 393-37-3, 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. 393-37-3, name is 5-Bromo-2-fluorobenzotrifluoride belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-(4-fluorophenyl)ethanol (1.02 g, 7.31 mmol, 1.2 equiv) in DMF (20 mL) was added KOtBu (0.96 g, 5.99 mmol, 1.4 equiv) and 4-bromo-1-fluoro-2-(tnfluoromethyl)benzene (1.48 g, 6.09 mmol, 1.2 equiv). After stirring 2 h, the reactionwas dilute with ether. The ether solution was washed with water, brine, dried (Na2SO4),and concentrated in vacuo. The crude product was purified by silica gel flashchromatography (0-30% EtOAc in hexane) to provide the product (1.36 g, 62%) as awhite solid. ?H NMR (500 MHz, CDC13) 7.69 (d, J= 2.5 Hz, 1H), 7.57 (dd, J= 8.8, 2.5 Hz, 1H), 7.28 – 7.25 (m, 2H), 7.02 (t, J=8.3 Hz, 2H), 6.85 (d, J 8.8 Hz, 1H), 4.21 (t, J6.5 Hz, 2H), 3.12 (t,J 6.5 Hz, 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, 5-Bromo-2-fluorobenzotrifluoride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 25017-13-4, A common heterocyclic compound, 25017-13-4, name is 1-(2-Bromoethyl)-3-fluorobenzene, molecular formula is C8H8BrF, 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 2-(9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl)-ethanesulfonic acid 4-cyano- benzylamide dihydrochloride (0.127 g, 0.30 mmol; prep P above), 1-(2- bromo-ethyl) -3-fluoro-benzene (0.064 g, 0.315 mmol) and potassium carbonate (0.145 g, 1.05 mmol) was added acetonitrile (4 mL) and water (0.1 mL). The mixture was stirred for 20 minutes before it was heated by microwave irradiation (10 minutes, 160C) and was then filtered and evaporated. The crude product was purified by chromatography on silica gel using methanol saturated with ammonia in dichloromethane as eluent, which afforded 43 mg (30.3%) of the title compound. ¹3C NMR (125.7 MHz, CDCl3) 8 163.90,161.94, 144.35,141.66, 132.65, 130.03,129.96, 128.11,123.86, 118.70,115.12, 114.95,113.51, 113.34, 111.76, 68.34, 60.85, 56.85, 56.41, 54.40, 47.82, 47.47, 31.35

The synthetic route of 25017-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/123748; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary