Author: Jessica.F

Electric Literature of 6683-75-6,Some common heterocyclic compound, 6683-75-6, name is 1,2-Dibromo-4-tert-butylbenzene, molecular formula is C10H12Br2, 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.

In a three-necked flask equipped with a reflux tube, 292 g (1.0 mol) of p-tert-butyl o-dibromobenzene was added.Potassium ferricyanide 329 g (1.0 mol), DBU 1460 mL, silver carbonate 16.8 g (0.1 mol) and copper acetylacetonate 52.4 g (0.2 mol),The reaction was heated to 100 C. After the reaction was over, insoluble material was filtered off and the DBU was recovered under reduced pressure. The residue was poured into water and filtered to obtain 180 g of p-tert-butylphthalonitrile, with a yield of 97.8% and a purity of 99.0%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dibromo-4-tert-butylbenzene, its application will become more common.

Reference:
Patent; Zhengzhou Gaike Technology Co., Ltd.; Guo Libing; (5 pag.)CN107903190; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 30273-22-4, name is 4-Bromo-2-ethylaniline hydrochloride, 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. HPLC of Formula: C8H11BrClN

Example 27 8-Bromo-6-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride Step A.; A solution of sodium nitrite (0.70 g, 10.2 mmol) and H2O (2.1 mL) was added dropwise at 0 C. to a solution of 4-bromo-2-ethylbenzenamine hydrochloride (2.0 g, 8.45 mmol) in 12N HCl (20.1 mL) and TFA (2.6 ml). The reaction mixture was stirred at 0 C. for 1 h followed by the dropwise addition of a solution of tin(II)chloride (3.53 g, 18.6 mmol) in 12N HCl (5.0 mL) and H2O (0.7 mL) at 0 C. The reaction mixture stirred for 15 h at 20 C. and was filtered to give 1-(4-bromo-2-ethylphenyl)hydrazine hydrochloride as an off-white solid (2.9 g, 11.5 mmol).

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

Reference:
Patent; Bristol-Myers Squibb Company; US2007/27178; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 5279-32-3, These common heterocyclic compound, 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, 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.

Step 1, Method 25: ll-(2-Chlorophenyl)-4,6,10-trioxa-12- azatricyclo[7.3.0.03’7]dodeca-l,(9),2,7,ll-tetraene[0251] A mixture of 5,6-dibromo-2H-l,3-benzodioxole (500 mg, 1.79 mmol), 2- chlorobenzamide (300 mg, 1.93 mmol), potassium carbonate (1.0 g, 7.24 mmol), N,N-dimethylethane-l,2-diamine (50 mu,, 0.57 mmol) and copper(I) iodide (35 mg, 0.18 mmol) in toluene (30 mL) and 1,4-doxane (30 mL) was stirred under reflux for 24 hours. After cooling to room temperature the mixture was diluted with ethyl acetate (50 mL), filtered and concentrated. The residue was taken up in ethyl acetate (150 mL), washed with water (50 mL) and brine (50 mL), dried over magnesium sulphate, filtered and absorbed onto a small amount of silica. Purification by FCC (silica, 0-20% ethyl acetate in heptane) and recry stallis ation from 5% ethyl acetate in heptane (10 mL) gave the title compound 120 mg (25% yield) as a colourless, crystalline solid. 5H MR (500 MHz, DMSO) 8.09 (dd, J = 7.7, 1.8 Hz, 1H), 7.69 (dd, J = 7.9, 1.2 Hz, 1H), 7.59 (td, J = 7.7, 1.8 Hz, 1H), 7.55 (td, J = 7.5, 1.3 Hz, 1H), 7.51 (s, 1H), 7.41 (s, 1H), 6.14 (s, 2H). Tr(MET-uHPLC-AB-lOl) = 3.66 min, (ES+) (M+H)+274.

The synthetic route of 5279-32-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; BROWN, Christopher, John; PRIME, Michael, Edward; WEDDELL, Derek, Alexander; WALTER, Daryl, Simon; GILES, Paul, Richard; WIGGINTON, Ian, James; TAYLOR, Malcolm, George; GALAN, Sebastien, Rene, Gabriel; JOHNSON, Peter, David; KRUeLLE, Thomas, Martin; MORAO, Inaki; CLARK-FREW, Daniel; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; (120 pag.)WO2016/33460; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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