Month: July 2021

Reference of 13194-73-5,Some common heterocyclic compound, 13194-73-5, name is 3,5-Dibromo-4-methylaniline, molecular formula is C7H7Br2N, 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.

Example 29 1,3-Dibromo-2-methylbenzene A solution of (3,5-dibromo-4-methylphenyl)amine dissolved in water (80 mL) and concentrated HCl (7.5 mL) stirring for 20 min, then the mixture was cooled to 0~5 C., and the solution of NaNO2 (3.4 g/30 mL H2O) was added. The reaction mixture was stirred for 2 h at 0~5 C., then the suspension was added to hypophosphorous acid solution (50%, 27.9 g), which was cooled to 0 C. The mixture was stirred at room temperature overnight. Then it was extracted with CH2Cl2 (100 mL*2) and the combined organic layers were washed with brine (30 mL) and dried over Na2SO4. After silica column chromatography, (eluted with petroleum ether), 3.57 g product was obtained, as colorless liquid. 1H NMR (400 MHz, CDCl3): delta 2.57 (s, 3H), 6.89 (t, J=8.0 Hz, 1H), 7.50 (d, J=8.0 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dibromo-4-methylaniline, its application will become more common.

Reference:
Patent; Glaxo Group Limited; US2009/197871; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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. Quality Control of 1-Bromo-3,4,5-trifluorobenzene

General procedure: To a mixture of 1,3,5-triazine(0.5 mmol), aryl halide (0.5 mmol), DMEDA (0.45 mmol)and K2CO3 (1 mmol) in MeCN (3 mmol) was added CuI (0.15mmol). The resulting mixture was stirred at reflux. After completionof the reaction, the reaction mixture was cooled to r.t.,concd NH3 (4 mL) and sat. NaCl (10 mL) were added, and theorganic phase was then extracted with EtOAc (3 × 15 mL). Theorganic phase was dried over anhyd Na2SO4. The crude residuewas obtained after evaporation of the solvent in vacuum, andthe residue was purified by flash chromatography with petroleumand EtOAc as the eluent to give the pure product. N2-(4-Methoxyphenyl)-N4,N4-dimethyl-6-phenyl-1,3,5-triazine-2,4-diamine (3a):

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 138526-69-9, its application will become more common.

Reference:
Article; Li, Jin Jing; Wu, Kong; Zhou, Wei; Wang, Hong; Cui, Dong-Mei; Zhang, Chen; Synlett; vol. 27; 13; (2016); p. 1993 – 1996;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 2695-47-8,Some common heterocyclic compound, 2695-47-8, name is 6-Bromo-1-hexene, molecular formula is C6H11Br, 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 70 ml oven dried autoclave containing a stirrer bar wascharged the AgI (0.5 mg, 0.002 mmol) and Cs2CO3 (978 mg, 3.0mmol). The autoclave was purged three time with CO2 and theterminal alkynes 1 (2.0 mmol), bromides 2 (3.0 mmol), and dryDMF (20 ml) were then added sequentially via a syringe. Theautoclave was then sealed and pressurized to the appropriatepressure with CO2. The reaction mixture was then stirred at 60C for 24 h and the autoclave was cooled to room temperatureand the remaining CO2 slowly vented from the system. Thereaction mixture was diluted with water (30 ml) and extractedwith ethyl acetate (30 ml × 3). The combined organic layerswere washed with water and brine, dried over Na2SO4, andfiltered. The solvent was removed under vacuum. The productwas isolated by column chromatography on silica gel.

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-1-hexene, its application will become more common.

Reference:
Article; Zhang, Linlin; Zhang, Wenzhen; Shi, Linglong; Ren, Xiang; Lue, Xiaobing; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 34; 6; (2013); p. 1179 – 1186;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 67344-77-8, 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. 67344-77-8 name is 1-(3-Bromophenyl)-N-methylmethanamine, 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.

To a solution of 1-benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester (1 mmol), (3-bromo-benzyl)-methyl-amine (1 mmol) in 2 mL of CH2Cl2 were added NaBH(OAc)3 (2 mmol) and 5 drops of AcOH, and the resulting mixture was stirred for 3 h. The mixture was treated with aq. NaHCO3, extracted by CH2Cl2 (3*5 mL), and the combined extracts were washed by brine (10 mL), dried over Na2SO4, and concentrated to give 261.3 mg of crude product in 65percent yield. MS m/e=403.3 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(3-Bromophenyl)-N-methylmethanamine, and friends who are interested can also refer to it.

Reference:
Patent; Han, Bo; Knust, Henner; Nettekoven, Matthias; Ratni, Hasane; Wu, Xihan; US2008/306086; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 10485-09-3, 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. 10485-09-3, name is 2-Bromoindene, This compound has unique chemical properties. The synthetic route is as follows.

Production Example 2 Synthesis of an Li salt of 2,2′-diindenyltetramethyldisilane In a 2L-three-neck flask, THF (300 ml) and Mg (25g, 1042 mmol) were incorporated. Further, 1,2-dibromoethane (0.1 ml) was added. The resultant was stirred at room temperature for 10 minutes, whereby the Mg surface was activated. To this, 2-bromoindene (100g, 513 mmol) which had been dissolved in THF (500 ml) was added dropwise by means of a pressure equalizing funnel. After cooling the resulting reaction mixture on ice bath, 1,2-dichlorotetramethyldisilane (46.8 ml, 251 mmol) was added dropwise. After stirring the reaction mixture for overnight, the solvent was distilled off. Extraction was conducted from the resulting solid by using hexane (500 ml * 2). By subjecting the resulting extraction solution to evaporation dryness, 2,2′-diindenyltetramethyldisilane was obtained as a pale yellow product (82g, 236 mmol, 92%).

The chemical industry reduces the impact on the environment during synthesis 2-Bromoindene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; YABUGAMI, Minoru; OKAMOTO, Takuji; EP2650300; (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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,3-Dibromo-5-fluorobenzene

To mixture of l,3-dibromo-5-fluorobenzene (LXXXVII) (100 g, 393 mmol) and N’,N’-dimethylethane-l,2-diamine (173 g, 1.97 mol, 214 mL) was added t-BuOK (88 g, 787 mmol) in one portion at 25C under N2. The mixture was stirred at 25C for 30 min, then heated to 110C and stirred for 11.5 h. The mixture was cooled to 25C and concentrated in reduced pressure at 45C. The residue was purified by silica gel chromatography (column height: 250 mm, diameter: 100 mm, 100-200 mesh silica gel, PE/EtOAc = 2: 1, Rf = 0.6) to give N1-(3-bromo-5-fluorophenyl)-N2,N2-dimethylethane-1,2-diamine (LXXXVIII) (30 g, 114.9 mmol, 29.2% yield) as a yellow oil. ESIMS found for CioHi4BrFN2 mlz 261.1 (M+H).

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 1435-51-4.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (265 pag.)WO2017/24010; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1074-24-4,Some common heterocyclic compound, 1074-24-4, name is 1,4-Dibromo-2,5-dimethylbenzene, molecular formula is C8H8Br2, 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.

A solution of 1,4-dibromo-2,5-dimethylbenzene (5.0 g, 18.94 mmol, Aldrich) in anhydrous THF (20 mL) was cooled to about -10° C. Isopropyl magnesium chloride (3.95 mL, 2.0 M in THF, 7.9 mmol) was added. The mixture was allowed to stir at about -10° C. for about 0.25 h. Next n-butyl lithium (6.31 mL, 2.5 M in hexanes, 15.8 mmol) was added dropwise keeping the temperature at or below about 0° C. Once the addition was complete the reaction was stirred at about -10° C. for about 1 h. Next a solution of DMF in 10 mL anhydrous THF (20.52 mmol) was added dropwise keeping the temperature at or below about 0° C. The reaction was stirred at ambient temperature for about 3 hours. The reaction was poured into about 50 mL of about 5 M aqueous citric acid solution (exothermic) and stirred at room temperature for about 10 minutes. The layers were separated and the aqueous layer was extracted once with toluene (50 mL). The combined organic layers were washed with water (20 mL), then concentrated in vacuo. The residue was purified by column chromatography (SiO2, diethyl ether/petroleum ether 5:95) to give 4-bromo-2,5-dimethylbenzaldehyde (3.66 g, 17.18 mmol, 91percent) as a pale crystalline solid: 1H-NMR (CDCl3, Bruker 400 MHz) delta 2.43 (3H, s); 2.60 (3H, s); 7.47 (1H, s); 7.63 (1H, s) 10.2 (1H, s).

The synthetic route of 1074-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; Cusack, Kevin P.; Gordon, Thomas D.; Hoemann, Michael Z.; Ihle, David C.; Li, Bin; Lo Schiavo, Gloria Y.; Somal, Gagandeep K.; Friedman, Michael; Hayes, Martin E.; Bakker, Wouter Iwema; US2014/179676; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 327-52-6, 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 327-52-6 as follows.

N2 Protected, single-neck flask in 20ml inputs 0.4g Dppp (0.001mol, 0.1eq), 0.11g (0.0005mol, 0.05eq) of palladium acetate, acetonitrile 3g, purged three times with stirring, heated in a water bath warmed to 58 ~ 62 , for 2.5 to 3.5 hours. document.write(“”); Incubation was completed, was cooled to 30 ~ 35 , a catalyst. document.write(“”); N 2Protected, into two flasks in 50ml of 1.4g (0.01mol, 1.0eq) and itaconic acid monomethyl ester, acetonitrile 10g, stirring and mixing uniformly; was added DBU: 3.8g (0.025mol, 2.5eq), a clear solution; 2,4,5-trifluoro-bromobenzene was added: 2.32g (0.011mol, 1.1eq), stirring; N2 of replacement three times, the catalyst prepared above was added, N 2Substituted three times, under N2 protection, reaction at 80 24 hours. TLC Bi insulation test point to the raw material disappears, the reaction was complete. The reaction solution (10 mL x 3) and washed with 13% brine, dried over sodium sulfate, filtered and concentrated to a crude product of Formula 3 compounds done, purified through the column to obtain 2.3g, Yield: 83.9%. document.write(“”); Preparation of Compound 4: Example 2

According to the analysis of related databases, 327-52-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZHEJIANG JIUZHOU PHARMACEUTICAL CO., LTD; ZHU, GUOLIANG; HE, QIAN; QIAN, LINGFENG; XU, YINGZHOU; YAN, PUZHA; (11 pag.)CN106146340; (2016); A;,
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. 3344-70-5, name is 1,12-Dibromododecane, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C12H24Br2

General procedure: The new inhibitors (3-22; Fig. 3) were prepared via standard synthetic strategy [24] and [25]. The solution of isoquinoline (1.6 g, 12.4 mmol) and corresponding alkylating agent (5.6 mmol) in DMF (10 ml) was stirred at 70 °C. The reaction mixture remained at the room temperature. It was portioned with acetone (50 ml) and cooled in refrigerator (5 °C) overnight. The crystalline or amorphous crude product was collected by filtration, washed with acetone (3 .x. 20 ml) and recrystallized from MeCN. NMR, ESI-MS and elemental analysis determined the entity and purity of all prepared compounds.

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 3344-70-5.

Reference:
Article; Musilek, Kamil; Komloova, Marketa; Holas, Ondrej; Hrabinova, Martina; Pohanka, Miroslav; Dohnal, Vlastimil; Nachon, Florian; Dolezal, Martin; Kuca, Kamil; European Journal of Medicinal Chemistry; vol. 46; 2; (2011); p. 811 – 818;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 3638-73-1, A common heterocyclic compound, 3638-73-1, name is 2,5-Dibromoaniline, molecular formula is C6H5Br2N, 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.

Sodium nitrite (65.2 mmol) was added in several portions to a solution of 2,5- dibromobenzenamine (55.8 mmol) in trifluoroacetic acid (80 mL) at 0 C. The resulting solution was added to a boiling solution of sodium sulfate (10 g) in 50% sulfuric acid (120 mL) and the reaction mixture was maintained at reflux for 1 h. Then the product was steam-distilled and the distillate was extracted with dichloromethane (2 x 200 mL). The combined organic layers were dried (sodium sulfate) and concentrated to provide 2,5-dibromophenol in 41% yield as a yellow solid.

The synthetic route of 3638-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2009/23844; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary