Month: September 2021

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 2789-89-1 as follows. COA of Formula: C14H8Br2

General procedure: The photocatalyst [Ir(dF-CF3-ppy)2(dtbpy)]PF6 (PC-1) (11.2 mg, 0.01 mmol, 2.0 mol%) wasadded to an oven-dried Schlenk tube containing a magnetic stirring bar and anhydrous ethylacetate (2.5 mL, 0.2 M) was added under argon. In the absence of light, the enone (0.5 mmol,1.0 equiv) and the alkyne (1.0 mmol, 2.0 equiv) were added under an argon stream. Theresulting solution was degassed using three freeze-pump-thaw cycles and the tube was finallybackfilled with argon. The reaction mixture was allowed to stir at room temperature for 24 hunder irradiation with visible light from two 30 W Kessil LEDs (lambdamax = 455 nm, see chapter 1.2).The solvent was evaporated and the crude reaction products were purified by columnchromatography over silica gel (dry load of crude material, pentane/EtOAc or pentane/diethylether mixtures as eluent) to afford products 6a-6e, 9a-9e and 10.

According to the analysis of related databases, 2789-89-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Strieth-Kalthoff; Henkel, Christian; Teders, Michael; Kahnt, Axel; Knolle, Wolfgang; Gomez-Suarez, Adrian; Dirian, Konstantin; Alex, Wiebke; Bergander; Daniliuc, Constantin G.; Abel; Guldi, Dirk M.; Glorius; Chem; vol. 5; 8; (2019); p. 2183 – 2194;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 13633-25-5, These common heterocyclic compound, 13633-25-5, name is 1-Bromo-4-phenylbutane, 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: A solution of ethyl-2-(diethoxyphosphoryl) acetate 5 in DMF(25 mL/mol) was stirred at 0 C. The base was added and the solutionwas continued to stir for 20 min before the alkyl halide wasadded drop wise. The reaction mixture was allowed to warm toroom temperature and then heated at 60 C for 18 h. After coolingthe reaction mixture was acidified with 10% citric acid andextracted with diethyl ether (3 x 30 mL). The combined organicphases were washed with H2O (3 x 30 mL), brine (1 30 mL) anddried over Na2SO4. The product 6a-c was purified with columnchromatography using 2:1 diethyl ether/pentane as eluent.

Statistics shows that 1-Bromo-4-phenylbutane is playing an increasingly important role. we look forward to future research findings about 13633-25-5.

Reference:
Article; Skagseth, Susann; Akhter, Sundus; Paulsen, Marianne H.; Muhammad, Zeeshan; Lauksund, Silje; Samuelsen, Ørjan; Leiros, Hanna-Kirsti S.; Bayer, Annette; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 159 – 173;,
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. 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, A new synthetic method of this compound is introduced below., name: (4-Bromo-2-fluorophenyl)methanamine

Step 1: (4-Bromo-2-fluorophenyl)methanamine (924 mg, 4.53 mmol) was dissolved in pyridine and ethane sulfonyl chloride (0.82 mL, 8.60 mmol) was added to the solution at 0 C. The mixture was stirred for 1 h at 0 C. Then, the mixture was quenched with 1N HCl and extracted with ethyl acetate. Drying over magnesium sulfate and evaporation of the ethyl acetate and purified by column chromatography gave N-(4-bromo-2-fluorobenzyl)-ethanesulfonamide in pure form (1.06 g, 79%).

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; Gruenenthal GmbH; FRANK, Robert; Bahrenberg, Gregor; Christoph, Thomas; Lesch, Bernhard; Lee, Jeewoo; US2013/79320; (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. 615-36-1, name is 2-Bromoaniline, A new synthetic method of this compound is introduced below., Computed Properties of C6H6BrN

General procedure: The 25 mL RB flask was charged with arylboronic acid (1 mmol), N-nucleophile (2 mmol), Ni(OAc)2*4H2O/1a (10 mol % of Ni(II) salt and 20 mol % of 1a), TMG (2 mmol), and toluene (1 ml). The reaction mixture was stirred at 60 C for 24 h. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL), and washed with brine water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using hexane to afford the Chan-Lam product in high purity.

The synthetic route of 615-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Keesara, Srinivas; Tetrahedron Letters; vol. 56; 48; (2015); p. 6685 – 6688;,
Bromide – Wikipedia,
bromide – Wiktionary

445-02-3, name is 4-Bromo-2-(trifluoromethyl)aniline, 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 4-Bromo-2-(trifluoromethyl)aniline

To a mixture of 2-amino-5-bromobenzotrifluoride (1 .0 g, 4.17 mmol) in DCM (10 mL) at 0-5C was added NEt3 (1 .16 mL, 8.33 mmol), then methanesulfonyl chloride (0.389 mL, 5 mmol) dropwise. The reaction mixture was stirred at rt for 4 days. After 2 days, more NEt3 was added (1 .16 mL, 8.33 mmol). As there was no evolution after 3 days, more NEt3 (0.580 mL, 4.17 mmol) and methanesulfonyl chloride (0.324 mL, 4.17 mmol) were added. The reaction was not completed, so the reaction mixture was then heated in a microwave oven at 1 10C for 20 min. There was no evolution, so the reaction was stopped. The reaction mixture was diluted with water and DCM. Layers were separated. The organic layer was washed with water, dried over MgS04 and evaporated. Purification by Flash chromatography using CombiFlash Companion ISCO system (Redisep silica 40g column, eluting with Cyclohexane/EtOAc 100:0 to 70:30) did not give the pure compound. Purification by prep HPLC using Gilson system (SunFire C18 column, eluting with H20 + 0.1 % TFA / CH3CN 20% to 85%) gave the title compound (404 mg, 31 % yield) as a white solid. 1 H-NMR (400 MHz, DMSO-d6, 298 K): ? ppm 3.12 (s, 3H) 7.55 (d, 1 H) 7.91 (d, 1 H) 7.92 (s, 1 H) 9.56 (s, 1 H). MS(10): 316.3-318.2 [M-1 ]

The synthetic route of 445-02-3 has been constantly updated, and we look forward to future research findings.

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;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 6698-13-1, A common heterocyclic compound, 6698-13-1, name is 4-Bromo-1,3-benzodioxole, molecular formula is C7H5BrO2, 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.

Tert-butyl piperazine-l-carboxylate (1.11 g, 5.97 mmol) was added to a solution of 4- bromobenzo[d][l,3]dioxole (1 g, 4.97 mmol ) in Toluene (15.0 ml). The resulting suspension was degassed using a stream of argon. Cesium carbonate (2.27 g, 558 mu, 6.96 mmol), racemic- 2,2 -bis(diphenylphosphino)-l, -binaphtyl (232 mg, 373 muiotaetaomicron, Eq: 0.075) and Palladium (II) Acetate (55.8 mg, 249 muiotaetaomicron,) were added to this mixture. The reaction was then heated at 100 C over night. The reaction was cooled to rt, 40ml of water was added and the mixture was extracted with Ethyl Acetate ( 2x 80ml). The organic layers were dried over MgS04 and concentrated under vacuum. The crude material was purified by flash chromatography (silica gel, 50g, 0% to 50% EtOAc in heptane). to yield tert-butyl 4-(benzo[d][l,3]dioxol-4-yl)piperazine-l- carboxylate as a white solid ( 1.15 g, 75%). MS (ISP) m/z = 307.4 [(M+H)+].

The synthetic route of 6698-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; RODRIGUEZ SARMIENTO, Rosa Maria; WICHMANN, Juergen; WO2012/110470; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 134168-97-1, These common heterocyclic compound, 134168-97-1, name is 3-Bromo-5-fluoroaniline, 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.

Intermediate S1: N-(3-bromo-5-fluorophenyl)methanesulfonamide A solution of commercially available 3-bromo-5-fluoroaniline (0.500 g, 2.64 mmol) in pyridine (9.4 mL) was cooled to 0 C. and methanesulfonyl chloride (0.265 mL, 3.43 mmol) was added drop-wise; the resulting solution was allowed to warm to room temperature and stirred for 2 h. The solvent was removed under reduced pressure and the crude was partitioned between EtOAc and aqueous 1N HCl. The organic phase was dried over sodium sulfate and the solvent was removed; the crude was purified by flash chromatography on Biotage silica gel SNAP cartridge (cyclohexane to cyclohexane_EtOAc=50:50) to afford title compound as a white solid (0.543 g, 2.03 mmol, 77% yield). MS/ESI+ not detectable [MH]+, Rt=0.91 min (Method A). 1H NMR (400 MHz, DMSO-d6) delta ppm 10.29 (s, 1H), 7.23-7.30 (m, 1H), 7.19 (s, 1H), 6.99-7.06 (m, 1H), 3.12 (s, 3H).

Statistics shows that 3-Bromo-5-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 134168-97-1.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; BIAGETTI, Matteo; ACCETTA, Alessandro; CAPELLI, Anna Maria; GUALA, Matilde; RETINI, Michele; US2015/361100; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 7051-34-5, 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. 7051-34-5 name is (Bromomethyl)cyclopropane, 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.

Reference Example 1-19; 2-(cyclopropylmethyO-l,3-dithiane-2-carboxylic acid ethyl esterSodium hydride (1.03 g) was suspended in toluene (40.0 mL), followed by adding a solution of ethyl l,3-dithiane-2-carboxylate (4.13 g) and (bromomethyl)cyclopropane (2.52 mL) in dimethylformamide (10 mL) to the suspension at 00C and stirring the mixture overnight at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. Insoluble matters were filtered out, and the filtrate was concentrated under reduced pressure to give the title compound (5.20 g) as a colorless oil. mass:247(M+l)+ .

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

Reference:
Patent; BANYU PHARMACEUTICAL CO.,LTD.; KAMEDA, Minoru; KOBAYASHI, Kensuke; NAKAMA, Chisato; ANDO, Makoto; SATO, Nagaaki; WO2010/126163; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 51554-93-9, name is 1-Bromo-4-octylbenzene, 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. Safety of 1-Bromo-4-octylbenzene

Synthesis Example 2 Synthesis of Exemplified Compound 4 In a nitrogen atmosphere, 10 ml (16 mmol) of a 1.6 M n-butyllithium/hexane solution is added to a 100-ml three-necked flask cooled to -80 C. This solution is cooled to -80 C., and then 10 ml of THF maintained at -60 C. is added dropwise thereto from a dropping funnel. Subsequently, 3.1 g (16 mmol) of 1-bromo-4-n-octylbenzene maintained at -60 C. is added dropwise to the mixture from a dropping funnel. This mixture is stirred for one hour at -40 C., and then a solution of 2.3 g (22 mmol) of trimethyl borate in THF (10 ml) maintained at -40 C. is added thereto from a dropping funnel. Thereafter, the mixture is slowly heated to 10 C. over 2 hours, and then 50 ml of a 10% aqueous solution of HCl at 0 C. is added thereto. The mixture is extracted with 100 ml of toluene. This extract is washed three times with 100 ml of purified water, and then is dried with sodium sulfate. Toluene is distilled off under reduced pressure, and 3.3 g of a residue is obtained. This residue is further washed with a mixed liquid of 100 ml of purified water and 100 ml of hexane, and thus 2.0 g of the compound V-a, which is 4-n-octylphenylboronic acid, is obtained. It is confirmed by 1H-NMR and IR that the compound is consistent with the intended product.

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

Reference:
Patent; FUJI XEROX CO., LTD.; US2010/276672; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 58971-11-2, 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. 58971-11-2, name is 3-Bromophenethylamine, This compound has unique chemical properties. The synthetic route is as follows.

4i was then obtained by following the general procedure. A solution of compound 3 (140 mg, 0.7 mmol) in n-BuOH (6 mL) was treated with DIEA (98.6 mg, 0.77 mmol) and 3-bromophenethylamine (154 mg, 0.77 mmol). Compound 4i was purified from this crude material by column chromatography (silicagel, n-hexane/EtOAc=3:1) (128.2 mg, 50.7%). 1H-NMR (400 MHz, CDCl3) delta 7.71-762 (m, 2H), 7.49 (d, J=8.4 Hz, 1H), 7.38-7.30 (m, 2H), 7.14-7.08 (m, 1H), 5.99 (s, 1H, -NH), 3.86 (dd, J=12.4, 6.8 Hz, 2H, -CH2-), 2.94 (t, J=7.2 Hz, 2H, -CH2-). 13C-NMR (100 MHz, CDCl3) delta 159.8, 156.7, 149.8, 147.2, 140.9, 139.9, 132.6, 130.9, 129.3, 128.9, 126.5, 125.3, 121.8, 119.6, 112.2, 41.3, 33.7. LC-MS (ESI) m/z: 362.0 ([M+H]+);

The chemical industry reduces the impact on the environment during synthesis 3-Bromophenethylamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; The Board of Regents of the University of Oklahoma; Wang, Weidong; Lee, Jae Wook; (35 pag.)US2019/47988; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary