Month: May 2021

These common heterocyclic compound, 24596-19-8, name is 4-Bromo-2,6-dimethylaniline, 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. category: bromides-buliding-blocks

4-Bromo-2,6-dimethylaniline (6.00 g, 30 mmol) was suspended in 48% HBr aqueous solution (20 mL), NaNO 2 (2.28 g, 33 mmol) dissolved in water at -10 C. was added and stirred for 1 hour And sulfamic acid (0.58 g, 6 mmol) was added. This was treated with FeSO 4 .7H 2 O (4.17 g, 15 mmol) in 48% HBr aqueous solution (20 mL) and heated gradually to 80 C., and the mixture was stirred at 80 C. for 1 hour. Water was added to the mixture, the mixture was extracted with hexane, and the organic phase was dried with anhydrous Na 2 SO 4, then the solvent was removed under reduced pressure. Purification with medium pressure (silica gel, hexane) gave 2,5-dibromo-m-xylene (6.19 g, 72% yield).

The synthetic route of 4-Bromo-2,6-dimethylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; National University University of Tokyo; Hanaoka, Kenjiro; Urano, Yasuteru; Takahashi, Shoudai; (48 pag.)JP2018/90536; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 3722-78-9, 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. 3722-78-9 name is 8-Bromochroman, 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.

EXAMPLE 22 Trans-2-[4-(3,4-dihydro-2H-chromen-8-yl)-1,2,3,6-tetrahydropyrid-1-yl]-5-fluoroindan-1-ol Prepared using, in succession, the methods described in Examples 18 and 19, but using 8-bromo-3,4-dihydro-2H-chromene in Step 1 of Example 18, and using 2-bromo-5-fluoro-indan-1-one in Step 2 of Example 18.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Bromochroman, and friends who are interested can also refer to it.

Reference:
Patent; Adir et Compagnie; US5958927; (1999); A;,
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. 26177-44-6, name is (4-Bromophenyl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H9BrClN

A slightly yellow solution of 2,5-difluoro-4-(trifluoromethyl)aniline (10.0 ml; 76.708 mmol) in MeCN (90 ml) was treated with copper(ll) bromide (17.133 g; 76.708 mmol), and the green heterogeneous mixture was heated to 45C. A solution of tert-butyl nitrite (10.0 ml; 84.379 mmol) in MeCN (20 ml) was then added dropwise over 30 min., and the resulting mixture was further stirred at 45C for 2h30. The dark-green heterogeneous reaction mixture was allowed to cool to rt, and was directly purified by FC (DCM). After concentration to dryness under reduced pressure, the expected product 1-bromo-2,5-difluoro-4-trifluoromethyl- benzene was obtained as an orange oil (10.290 g; 51 %). LC-MS: tR = 1.07 min.; [M+H]+: no ionisation.

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; ACTELION PHARMACEUTICALS LTD; WO2008/78291; (2008); 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. 89523-51-3, name is 5-Bromobenzo[c]phenanthrene, A new synthetic method of this compound is introduced below., SDS of cas: 89523-51-3

a) Synthesis of benzo[c]phenanthrene-5-boronic acid 52 ml (130 mmol) of n-buthyllithium (2.5 M in n-hexane) are added dropwise to a suspension of 30.7 g (100 mmol) of 5-bromobenzo[c]phenanthrene in 1000 ml of THF at -78 C. with vigorous stirring, and the mixture is stirred for a further 2 h. 16.7 ml (150 mmol) of trimethyl borate are added to the red solution in one portion with vigorous stirring, the mixture is stirred at -78 C. for a further 30 min., then warmed to room temperature over the course of 3 h, 300 ml of water are added, and the mixture is stirred for 30 min. The organic phase is separated off and evaporated to dryness in vacuo. The solid is taken up in 100 ml of n-hexane, filtered off with suction, washed once with 100 ml of hexane and dried in vacuo. Yield: 24.8 g (91 mmol), 91%, purity about 90% (NMR) of boronic acid, with varying amounts of boronic anhydride and boronic acid. The boronic acid can be used in this form without further purification.

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; Merck Patent GmbH; US2011/288292; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 376646-62-7, name is (4-Bromo-2-methylphenyl)methanamine, molecular formula is C8H10BrN, 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 (4-Bromo-2-methylphenyl)methanamine

[0115] To a solution of (4-bromo-2-methylphenyl)methanamine (1.2 g, 6 mmol) in DCM (30 mL) were added TEA (1.82 g, 18 mmol) and Boc20 (1.43 g, 6.6 mmol). The mixture was stirred at room temperature for 1 h. After diluted with water (50 mL), the mixture was extracted with DCM (50 mL x2). The combined organics were washed with brine (50 mL), dried (Na2S04), filtered and concentrated to give crude title product (1.7 g, yield 95%) as a white solid, which was used directly in the next step without further purification. ESI-MS (M+H)+: 300.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 376646-62-7, its application will become more common.

Reference:
Patent; BIOGEN MA INC.; MACPHEE, J. Michael; CHEN, Robbie; FERGUSON, Steven; FRANKLIN, Lloyd; MACK, Tamera, L.; (78 pag.)WO2016/201271; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 875664-41-8, 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. 875664-41-8 name is 3-Bromo-4,5-difluoroaniline, 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.

1 -methyl-4-[(3 -methyloxetan-3 -yl)sulfamoyl]pyrrole-2-carboxylic acid (200 mg, 0.73 mmol) was dissolved in N,N-dimethylformamide (2 mL). HATU (0.35 g, 0.91 mmol) was added followed by diisopropylethylamine (0.38 mL, 2.19 mmol). The resulting mixture was stirred for 30 minutes at room temperature. Then, 4-fluoro-3,5-dimethylaniline (0.2 g, 1.46 mmol) was added. The resulting mixture was stirred for 24 hours and next poured onto 10 mL of ice. The mixture was extracted using 2-Me-THF (3 x 10 mL). The combined organics were washed withbrine, dried on Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0:100). The desired fractions were concentrated in vacuo and dried in a vacuum oven at 55C for24 hours yielding compound 80 (130 mg):Compound 100 to 105 were prepared similarly as described for compound 80, using 1-methyl-4-[[(1 S)-2,2,2-trifluoro- 1 -methyl-ethyl]sulfamoyl]pyrrole-2-carboxylic acid instead of 1 -methyl-4-[(3 -methyloxetan-3 -yl)sulfamoyl]pyrrole-2-carboxylic acid and the corresponding aniline instead of 4-fluoro-3 ,5 -dimethylaniline. After addition of the aniline, the mixture was stirred at 50C forhours instead of 24 hours at room temperature.Crude compound 100 was purified by silica gel chromatography heptane-EtOAc 100/0 to 0/100. The product was crystallized from diisopropylether (15 mL)/iPrOH (3.5 mL). The product wasfiltered off, washed with diisopropylether (3x), and dried at 50C in vacuo, resulting in compound 100 (251 mg). MethodA; Rt: 1.98 mi mlz: 489.8 (M-H) Exactmass: 491.0. ?HNMR (400 MHz, DMSO-d6) oe ppm 1.08 (d, J=6.8 Hz, 3 H), 3.84 – 4.00 (m, 4 H), 7.36 (d, J=2.0Hz, 1 H), 7.66 (d, J=1.8 Hz, 1 H), 7.80 – 7.93 (m, 2 H), 8.20 (br. s., 1 H), 10.31 (br. s., 1 H).?9FNMR (377 MHz, DMSO-d6) oe ppm -138.51 –138.34 (m, 1 F), -133.99 –133.81 (m, 1 F), -76.07 (d, J=7.9 Hz, 3 F). Differential scanning calorimetry: From 30 to 300 C at 10C/mm:peak at 199.0 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4,5-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 32863-30-2, name is 4-(Bromomethyl)benzo[c][1,2,5]oxadiazole, 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. Formula: C7H5BrN2O

Compound 9-2 (44.5 mg, 0.1 mmol) and 4-(bromomethyl)benzo[c][1,2,5]oxadiazole 14-1 (32 mg, 0.15 mmol) were dissolved in dry DMF Add cesium carbonate (65.2mg, 0.2mmol) and stir at room temperature for about two hours. The reaction is complete. the reaction solution was extracted with water and ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous sodium sulfate. PE: EA = 5: 1 to give 20 mg of compound 14-2.

The synthetic route of 4-(Bromomethyl)benzo[c][1,2,5]oxadiazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhang Ao; Geng Meiyu; Song Zilan; Ai Jing; Gu Wangting; Liu Bo; Ding Jian; (28 pag.)CN110240587; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 21865-50-9,Some common heterocyclic compound, 21865-50-9, name is 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole, molecular formula is C12H12BrN, 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. 6-Bromo-9-ethyl-2,3,4,9-tetrahydro-1H-carbazole; A 500-mL round-bottomed flask was charged with 3-bromo-6,7,8,9-tetrahydro-5H-carbazole (5 g, 20.08 mmol, 1.00 equiv) in N,N-dimethylformamide (270 mL). To this solution was added sodium hydride (1.2 g, 30.00 mmol, 1.50 equiv, 60%) in several batches at -10 C., followed by addition of iodoethane (6.26 g, 40.13 mmol, 2.00 equiv) as a solution in N,N-dimethylformamide (30 mL) drop wise -10 C. The resulting mixture was stirred at room temperature for 30 minutes. The reaction progress was monitored by TLC (EtOAc:PE=1:1). Upon completion, the reaction was then quenched by the addition of water/ice (120 mL). Then, the mixture was extracted with ethyl acetate (4×80 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator. The residue was purified by a silica gel column chromatography eluted with ethyl acetate/petroleum ether (1/20) affording 3-bromo-9-ethyl-6,7,8,9-tetrahydro-5H-carbazole as brown oil (5 g, 90%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole, its application will become more common.

Reference:
Patent; Kalypsys, Inc; US8080566; (2011); B1;,
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. 392-83-6, name is 2-Bromobenzotrifluoride, A new synthetic method of this compound is introduced below., Recommanded Product: 392-83-6

General procedure: A test tube equipped with a magnetic stir bar was charged with an aryl halide(aryl halide, 1 mmol),CuSO4.5H2O(12.5 mg, 0.05 mmol),KOH (280 mg, 5 mmol) orCs2CO3 (1.62 g, 5 mmol), DMSO (2 mL), and water (0.2 mL; water was not used in case of using Cs2CO3 as base).After flushing with argon, 1,2-ethanedithiol (0.18 mL, 2 mmol) was added.The mixture was heated in a preheated oil bath for 20 hours90 C or 110 C bath which is pre-heated with agitation.After cooling to ambient temperature, the reaction mixture was distributed in aqueous HCl (5%) and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography (EtOAc / n-Hexane) to give the aryl thiol (see Table 2 below).

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; SUNGSHIN WOMEN`S UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; CHAE, Junghyun; Liu, Ya jun; KIM, Ji hye; (18 pag.)KR2017/76524; (2017); A;,
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. 41825-73-4, name is 2-Bromo-4,6-dimethylaniline, A new synthetic method of this compound is introduced below., SDS of cas: 41825-73-4

N-(2-Bromo-4,6-dimethylphenyl)(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilanamine Under an argon atmosphere, to a solution of 14.8 g (74.2 mmol) of 2-bromo-4,6-dimethylaniline in 200 ml of THF, 29.7 ml of 2.5 M (74.2 mmol) nBuLi in hexanes was added at -80 C. This mixture was warmed for ca. 1 hour to ambient temperature. Then, the resulting solution was added dropwise over ca. 1 hour, while vigorously stirring, to a solution of 18.0 g (74.2 mmol) of chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane in 100 ml of THF. The resulting mixture was stirred overnight at ambient temperature, and then, evaporated to dryness. To the residue, 150 ml of toluene was added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 168-172 C./0.2 mm Hg. The product crystallizes slowly at ambient temperature. Yield 16.5 g (55%). Anal. calc. for C19H24BrNSSi: C, 56.14; H, 5.95. Found: C, 56.28; H, 6.09. 1H NMR (CDCl3): delta 7.20 (d, J=4.9 Hz, 1H, 3-H in cyclopenta[b]thiophene), 7.18 (m, 1H, 3-H in phenyl), 6.97 (d, J=4.9 Hz, 1H, 2-H in cyclopenta[b]thiophene), 6.85 (m, 1H, 5-H in phenyl), 3.59 (br.s, 1H, 6-H in cyclopenta[b]thiophene, 2.92 (br.s, 1H, NH), 2.21 (s, 3H, 4-Me in phenyl), 2.19 (s, 3H, 6-Me in phenyl), 2.13 (s, 3H, 4-Me in cyclopenta[b]thiophene), 2.10 (s, 3H, 5-Me in cyclopenta[b]thiophene), 0.14 (s, 3H, SiMeMe’), 0.06 (s, 3H, SiMeMe’). 13C NMR (CDCl3): delta 152.2, 140.7, 140.0, 139.2, 132.6, 132.4, 131.2, 131.1, 130.0, 126.2, 119.9, 118.0, 49.2, 20.8, 20.6, 15.4, 12.1, -1.8, -2.1.N-(2-Bromo-4,6-dimethylphenyl)(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilanamine Under and argon atmosphere, to a solution of 14.8 g (74.2 mmol) of 2-bromo-4,6-dimethylaniline in 200 ml of THF, 29.7 ml of 2.5 M (74.2 mmol) nBuLi in hexanes was added at -80 C. This mixture was warmed for ca. 1 hour to ambient temperature. Then, the resulting solution was added dropwise for ca. 1 hour while vigorously stirring to a solution of 18.0 g (74.2 mmol) of chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane in 100 ml of THF. The resulting mixture was stirred overnight at ambient temperature, then, evaporated to dryness. To the residue, 150 ml of toluene was added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 168-172 C./0.2 mm Hg. The product crystallizes slowly at ambient temperature. Yield 16.5 g (55%). Anal. calc. for C19H24BrNSSi: C, 56.14; H, 5.95. Found: C, 56.28; H, 6.09. 1H NMR (CDCl3): delta 7.20 (d, J=4.9 Hz, 1H, 3-H in cyclopenta[b]thiophene), 7.18 (m, 1H, 3-H in phenyl), 6.97 (d, J=4.9 Hz, 1H, 2-H in cyclopenta[b]thiophene), 6.85 (m, 1H, 5-H in phenyl), 3.59 (br.s, 1H, 6-H in cyclopenta[b]thiophene, 2.92 (br.s, 1H, NH), 2.21 (s, 3H, 4-Me in phenyl), 2.19 (s, 3H, 6-Me in phenyl), 2.13 (s, 3H, 4-Me in cyclopenta[b]thiophene), 2.10 (s, 3H, 5-Me in cyclopenta[b]thiophene), 0.14 (s, 3H, SiMeMe’), 0.06 (s, 3H, SiMeMe’). 13C NMR (CDCl3): delta 152.2, 140.7, 140.0, 139.2, 132.6, 132.4, 131.2, 131.1, 130.0, 126.2, 119.9, 118.0, 49.2, 20.8, 20.6, 15.4, 12.1, -1.8, -2.1.

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; Voskoboynikov, Alexander Z.; Ryabov, Alexey N.; Nikulin, Mikhail V.; Lygin, Alexander V.; Uborsky, Dmitry V.; Coker, Catalina L.; Canich, Jo Ann M.; US2007/135623; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary