Tag: M.W=200-300

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

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

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 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

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

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

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. 2862-39-7, name is 2-Bromo-N,N-dimethylethanamine hydrobromide, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H11Br2N

General procedure: To the suspension of compound 11a-11e or 13 (1.5 mmol) inDCM (3 mL) was added TFA (3 mL). The mixturewas stirred at roomtemperature for 2 h and was concentrated under vacuum. Theproduct was then dissolved in DMF (6 mL) and added Et3N (1 mL)without further purification. The reaction mixture was stirred for1 h and was added CS2 (0.14 mL, 2.25 mmol) to continuously stir for 30 min. A series of different of halogen or alkene substitutedcompounds (1.5 mmol) were added respectively and the mixturewas stirred at 50 C overnight. The mixture was cooled to roomtemperature and extracted with dichloromethane (20 mL x 3). Theorganic phase was washed with brine (15mL x 3), dried overanhydrous Na2SO4 and concentrated under vacuum. The residuewas purified by column chromatography to provide the target products.

The synthetic route of 2862-39-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Su, Yue; Li, Ridong; Ning, Xianling; Lin, Zhiqiang; Zhao, Xuyang; Zhou, Juntuo; Liu, Jia; Jin, Yan; Yin, Yuxin; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 32 – 46;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 69321-60-4,Some common heterocyclic compound, 69321-60-4, name is 2,6-Dibromotoluene, molecular formula is C7H6Br2, 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 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was purged with nitrogen and charged with 2,6-dibromotoluene (2.50 g, 10.0 mmol), N-bromosuccinimide (1.78 g, 10.0 mmol) and carbon tetrachloride (40 iriL). The solution was heated to 80 C (oil bath temperature), and 2,2′-azobisisobutyronitrile (164 mg, 1.00 mmol) was added. The resulting mixture was refluxed for 14 h. After that time, the mixture was cooled to room temperature and filtered. The filter cake was washed with carbon tetrachloride (2 x 20 iriL). The filtrate was diluted with ethyl acetate (200 iriL) and washed with water (40 mL), saturated aqueous sodium bicarbonate (40 iriL) and brine (40 iriL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford a quantative yield (3.28 g) of l,3-dibromo-2-(bromomethyl)benzene as a yellow solid: mp 77-78 C; ]H NMR (300 MHz, CDC13) delta 7.55 (d, 2H, / = 8.1 Hz), 7.07 (t, IH, 7 = 8.1 Hz), 4.83 (s, 2H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Dibromotoluene, its application will become more common.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, 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: C6H2BrF3

Into a 100 mL three-necked flask were added 4.62 g 1-bromo-2,4,5-trifluorobenzene (0.022 mol) and anhydrous tetrahydrofuran (50 mL). The resulting mixture was cooled to -20 C. The solution of isopropylmagnesium bromide (22 mmol) in tetrahydrofuran (22 ml, 1M THF) was slowly added dropwise under nitrogen. After the addition was complete, the reactants were maintained at -20 C. for later use. Cuprous bromide-dimethyl sulfide (0.41 g, 0.002 mol) was suspended in 5 ml anhydrous tetrahydrofuran. The resulting mixture was cooled to -5 C. The Grignard reagent as described above was slowly added dropwise under nitrogen. After 15 min, a solution of the aziridine compound as shown in the above reaction formula (3.46 g, 0.015 mol) in 30 mL tetrahydrofuran was slowly added dropwise. After additional 5 min, 50 mL saturated solution of ammonia chloride was added to quench the reaction. Into this obtained solution was added 50 mL ethyl acetate. The separated water layer was extracted with another 50 mL ethyl acetate. The obtained organic layers were collected together and further washed with saturated solution of sodium chloride and then dried over anhydrous sodium sulfate, followed by filtration and concentration to obtain a crude product, which was further treated by column chromatography to obtain a compound (3.98 g, 0.011 mol, yield 73%). 1H NMR (400 MHz, CDCl3) delta 7.01 (t, J=10.5 Hz, 1H), 6.926.88 (m, 1H), 5.14 (d, J=12.6 Hz, 1H), 4.50 (s, 2H), 3.953.85 (m, 1H), 3.823.77 (m, 1H), 3.773.55 (m, 1H), 3.40 (s, 3H), 2.82 (s, 2H), 1.871.68 (m, 1H), 1.631.48 (m, 1H), 1.39 (s, 9H). Ms (M++1): 364.

The synthetic route of 1-Bromo-2,4,5-trifluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHEJIANG HISOAR PHARMACEUTICAL CO., LTD.; Pan, Xianhua; Li, Weijin; Zhang, Qunhui; Ruan, Libo; Yu, Wansheng; Deng, Fei; Ma, Tianhua; Huang, Mingwang; He, Minhuan; US2013/281695; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 4549-33-1,Some common heterocyclic compound, 4549-33-1, name is 1,9-Dibromononane, molecular formula is C9H18Br2, 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.

1,9-Dibromononane (610 muL, 3 mmol) was added to a stirred solution of the product of Preparation 1 (377 mg, 1 mmol) and DIPEA (1.05 mL, 6 mmol) in DMF (5 mL) at 50 C. The reaction mixture was heated at 80 C. for 72 h and then the solvent was removed under reduced pressure. The crude residue was purified by flash chromatography (10% MeOH in DCM containing 0.5% NH4OH) to give the title compound (292 mg, 0.5 mmol, 50%).

The synthetic route of 4549-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mammen, Mathai; Hughes, Adam; US2004/242622; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary