Tag: M.W=100-200

Reference of 74586-53-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 74586-53-1, name is 3-Bromo-5-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparative Example 1.1 N-(3-Bromo-5-methylphenyl)-4-(trifiuoromethyl)pyrimidin-2-amine A solution of 3-bromo-5-methylaniline (162.5 g, 874 mmol) in dioxane (2L) was prepared, and 2-chloro-4-(trifiuoromethyl)pyrimidine (182 g, 995 mmol) and methanesulfonic acid (97.5 g, 1.02 mol) were added sequentially. The resulting solution was heated to reflux overnight. The resulting mixture was cooled and concentrated under reduced pressure. The residue was diluted with water (2L), then adjusted to pH 7-8 with aqueous sodium bicarbonate solution, followed by extraction with EtOAc (2 x 2L) The organic layers were combined, washed with water (2 x 2 L), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford N-(3-bromo-5-methylphenyl)-4-(trifiuoromethyl)pyrimidin-2-amine (200 g, 602 mmol) as a light yellow solid. MS ESI [M + 3]+ 334.0. NMR (400 MHz, CDCI3): delta 8.68 (d, / = 4.9 Hz, 1 H), 7.79 (s, 1 H), 7.30 (s, 2 H), 7.10-7.06 (m, 2 H), 2.36 (s, 3 H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Bromo-5-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; MACHACEK, Michelle R.; ROMEO, Eric T.; KATTAR, Solomon D.; CHRISTOPHER, Matthew; ALTMAN, Michael D.; NORTHRUP, Alan B.; ELLIS, John Michael; BOYLE, Brendan O’; DONOFRIO, Anthony; GRIMM, Jonathan; REUTERSHAN, Michael H.; CHILDERS, Kaleen Konrad; OTTE, Ryan D.; CASH, Brandon; DUCHARME, Yves; HAIDLE, Andrew M.; SPENCER, Kerrie; VITHARANA, Dilrukshi; WU, Lingyun; ZHANG, Li; ZHANG, Peng; BEAULIEU, Christian; GUAY, Daniel; WO2014/48065; (2014); A1;,
Bromide – Wikipedia,
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Synthetic Route of 3814-30-0, The chemical industry reduces the impact on the environment during synthesis 3814-30-0, name is (Bromomethyl)cyclopentane, I believe this compound will play a more active role in future production and life.

EXAMPLE 2 Preparation of 1-cyclopentylmethylimidazole Imidazole (6.8 g, 0.1 mol) was added to a solution of sodium (2.3 g, 0.1 mol) in dry ethanol (100 ml). This solution was stirred and heated to reflux when bromomethylcyclopentane (16.3 g, 0.1 mol) was added dropwise. Following the addition, the mixture was stirred and heated under reflux for 16 h. After cooling, the reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was dissolved in 2 M-hydrochloric acid (150 ml) and the solution washed with ether. The aqueous solution was basified with 10 M-sodium hydroxide solution, and the product extracted with chloroform (3*50 ml). The extracts were combined, dried (MgSO4), and the solution concentrated to afford a yellow oil. The oil was purified using a silica gel column and elution with ethyl acetate/methanol (9:1). The product fractions were combined and concentrated under reduced pressure to afford 1-cyclopentylmethylimidazole (1.9 g), which was further purified by distillation, b.p. 68-69/0.125 mmHg.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, (Bromomethyl)cyclopentane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Burroughs Wellcome Co.; US4317830; (1982); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 4117-09-3, name is 7-Bromo-1-heptene, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 4117-09-3, Safety of 7-Bromo-1-heptene

Typical procedure for the preparation of Grignard reagent: To a suspension of magnesium (0.13g, 5.32mmol) in anhydrous THF (1mL) was added dropwise 1-bromobutane (0.1g, 0.71mmol) at room temperature under an argon. After the reaction started, a THF solution of the remaining 1-bromobutane (0.57g, 4.19mmol/anhydrous THF 4mL) was dropwise into the reaction mixture at that temperature. After stirring for 50min, 0.8M of n-BuMgBr in THF was obtained. (The concentration was determined by the titration experiment.) (0038) Method A: To a suspension of CuCN (0.059g, 0.66mmol) in anhydrous THF (1mL) was added dropwise a THF solution of n-BuMgBr (0.8M, 0.83mL, 0.66mmol, prepared from n-BuBr and magnesium) at -78C under argon. After stirring for 5min, the mixture was warmed to -10C, and then stirred for 10min. The reaction mixture was again cooled to -40C, and to this mixture was added dropwise a solution of (E)-diethyl 2-fluoro-3-phenyl-2-propenylphosphate (0.086g, 0.3mmol) in anhydrous THF (2mL). After 15min, the reaction was quenched with an aqueous saturated NH4Cl solution and the whole was extracted with diethyl ether. The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo. The residue was purified by silica gel column chromatography to give 2-fluoro-3-phenyl-1-heptene (13a) (quant., 19F NMR yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Bromo-1-heptene, and friends who are interested can also refer to it.

Reference:
Article; Nihei, Takashi; Kubo, Yusuke; Ishihara, Takashi; Konno, Tsutomu; Journal of Fluorine Chemistry; vol. 167; (2014); p. 110 – 121;,
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Related Products of 7073-94-1, A common heterocyclic compound, 7073-94-1, name is 1-Bromo-2-isopropylbenzene, molecular formula is C9H11Br, 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.

l-Bromo-2-Isopropylbenzene (6.0 g, 30 mmol) was dissolved in dry toluene (70 mL), and ethyl cyanoacetate (6.8 g, 60 mmol) and sodium phosphate (15 g, 90 mmol) were added. The reaction mixture was degassed by bubbling with argon gas. Bis(dibenzylideneacetone) palladium(O) (0.35 g, 0.60 mmol) and tri-tert-butylphosphine (0.25 g, 1.2 mmol) were added. The reaction mixture was charged in a 500 mL sealed tube and heated to 90 C for 20 hours. The reaction was cooled to room temperature and filtered through a Celite pad. The filtrate was concentrated and the residue was dissolved in ethyl acetate (120 mL) followed by a washing with water (2 x 100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography provided the title molecule as a colorless liquid (4.4 g, 63%): XH NMR (400 MHz, CDCI3) delta 7.44 (d, J = 7.6 Hz, 1H), 7.38-7.36 (m, 2H), 7.24-7.22 (m, 1H), 4.97 (s, 1H), 4.30-4.21 (m, 2H), 3.14 (hep, J = 5.2 Hz, 1H), 1.30-1.23 (m, 9H); EIMS m/z 216 ([M-CH3]+).

The synthetic route of 7073-94-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; GIAMPIETRO, Natalie C.; BAUM, Erich W.; FISCHER, Lindsey G.; GOLDSMITH, Miriam E.; CROUSE, Gary D.; RENGA, James M.; SPARKS, Thomas C.; (234 pag.)WO2016/99929; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1003-99-2, These common heterocyclic compound, 1003-99-2, name is 2-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.

The N-(t-butyloxycarbonyl)-4-piperidone (10.13 g, 50.8 mmol, 1.0 eq) and the 2-bromo-5-fluoroaniline (11.6Og, 61.0 mmol, 1.2 eq.) were weighed into a flask. Acetic acid (75 mL) was added, followed by trimethylsilyl cyanide (7.75 mL, 58.1 mmol, 1.14 eq.). The mixture was stirred at rt for 24 hr, and was then added to a mixture of 200 mL ice and 200 mL saturated ammonium hydroxide solution. The resulting mixture was extracted twice with methylene chloride, and the organic solution was dried over magnesium sulfate, filtered, and concentrated to provide 22.57g of crude product.

Statistics shows that 2-Bromo-5-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 1003-99-2.

Reference:
Patent; MERCK & CO., INC.; SUNESIS PHARMACEUTICALS, INC.; WO2006/44497; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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 206 4-(3-Bromo-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrile A mixture of 3.52 g (9.7 mmol) of 4-chloro-7-methoxy-6-nitro-3-quinolinecarbonitrile and 2.0 g (10.7 mmol) of 3-bromo-4-fluoro aniline in 150 ml of methoxyethanol was refluxed under nitrogen for 5.5 hours. The reaction mixture was diluted with ethyl acetate and wash with sodium bicarbonate solution and sodium chloride solution. The organic layer was dried with sodium sulfate and then solvent was removed under vacuum. The residue was chromatographed on silica gel eluding with mixture of ethyl acetate and methanol to give 3 g of yellow solid: mass spectrum (electrospray, m/e): 416.8 and 418.8.

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

Reference:
Patent; American Cyanamid Company; US6384051; (2002); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 766-46-1, 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. 766-46-1 name is 2′-Bromophenylacetylene, 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.

General procedure: All homocoupling reactions of aromatic terminal alkyneswere carried out under air. A mixture of aromatic terminal alkyne (1.0 mmol), NEt3 (1.0 mmol) and P-O coordinatedcyclopalladated complex 1 (0.005 mmol)/AgNO3 (0.5 mmol) inTHF:H2O (in 4:1 proportion, 2.5 mL) was allowed to react at60C. The reaction progress was analyzed by GLC. The mixturewas added brine (4 mL) and extracted three times with ethylacetate (3 × 15 mL), dried over Na2SO4, concentrated in vacuoand purifed by thin layer chromatography. The purifed products were identifed by 1H-NMR and 13C-NMR spectroscopy.The Supplemental Materials presents sample 1H and 13C NMRspectra of the diyne products (Figures S1-S24).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2′-Bromophenylacetylene, and friends who are interested can also refer to it.

Reference:
Article; Chen, Bo; Guo, Mengping; Wen, Yongju; Shen, Xiuli; Zhou, Xiuling; Lv, Meiyun; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 192; 3; (2017); p. 259 – 263;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 17247-58-4, name is (Bromomethyl)cyclobutane, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 17247-58-4, Product Details of 17247-58-4

A solution of 12.3 g (83 mmol) of cyclobutylcarbinyl bromide (Aldrich) and 13.7 g (91 mmol) of sodium iodide in 150 mL of acetone was heated to reflux overnight and then cooled to room temperature. The inorganic solids were removed by filtration and the acetone and cyclopropylcarbinyl iodide (8.41 g, 46%) were removed by distillation (ambient temperature and 150 torr at 80 C., respectively). A solution of 4.0 g (21.98 mmol) of cyclobutyl carbinyl iodide in 30 mL of anhydrous diethyl ether cooled to -78 C. was cannulated into a solution of 17 mL (21.98 mmol) of 1.3M sec-butyllithium in cyclohexanes and the solution was stirred for 5 minutes. To this mixture was cannulated a solution of 3.0 g (21.98 mmol) of freshly distilled sulfuryl chloride in 110 mL of hexanes cooled to -78 C., the mixture warmed to room temperature over 1 hour and was then carefully concentrated in vacuo. This mixture was redissolved in diethyl ether, washed once with some ice-cold water, dried (MgSO4), filtered, and concentrated carefully. This mixture was redissolved in 30 mL of THF, added dropwise to 500 mL of saturated NH3 in THF and was allowed to stir overnight. The mixture was concentrated in vacuo to a crude yellow solid and was recrystallized from the minimum amount of dichloromethane in hexanes with 1-2 drops of methanol to afford 1.39 g (42%) of cyclobutyl carbinylsulfonamide as a white solid. 1H NMR (CDCl3) delta 1.81-2.03 (m, 4H), 2.14-2.28 (m, 2H), 2.81-2.92 (m, 1H), 3.22 (d, J=7 Hz, 2H), 4.74 (brs, 2H); 13C NMR (CDCl3) delta 19.10, 28.21, 30.64, 60.93; MS m/e 148 (M-1)-. time: 1.73, method B), 818 (M++H)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/14173; (2008); 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. 55289-36-6, name is 3-Bromo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H8BrN

A mixture of sodium 2-(3-methoxypyridin-2-yl)acetate (0.166 g, 0.871 mmol), 3- bromo-2-methylaniline (0.1 18 mL, 0.958 mmol), DIEA (0.608 mL, 3.48 mmol) and HATU (0.397 g, 1.045 mmol) in DMF (4.0 mL) was stirred at room temperature. After 1 h, the mixture was diluted with EtOAc and washed twice with 10% aqueous LiCl, then with brine, dried and concentrated. The residue was purified by column chromatography on silica gel to provide N-(3-bromo-2-methylphenyl)-2-(3-methoxypyridin-2-yl) acetamide as a pale yellow solid (0.213 g, 73% yield). Mass spectrum m/z 335, 337 (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 55289-36-6.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; KO, Soo Sung; BATT, Douglas A.; BERTRAND, Myra Beaudoin; DELUCCA, George V.; LANGEVINE, Charles M.; LIU, Qingjie; SRIVASTAVA, Anurag S.; WATTERSON, Scott Hunter; WO2014/210087; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 7051-34-5,Some common heterocyclic compound, 7051-34-5, name is (Bromomethyl)cyclopropane, molecular formula is C4H7Br, 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.

4-Hydroxybenzaldehyde (3.00 g, 0.0246 mol), bromomethylcyclopropane (3.58 ml, 0.0369 mol) and K2CO3 (6.8 g, 0.050 mol) were taken in acetone (80 ml) and refluxed for 24 h. The reaction mixture was cooled to room temperature, the insolubles filtered through Celite and the solvent was evaporated to obtain a crude residue. Purification of the residue by column chromatography (silica gel 60-120 mesh, EtOAc:Hexane 0.5:9.5) afforded 3.6 g (83.14%) of 4-cyclopropylmethoxybenzaldehyde. LCMS [M+H]+ 177.0 IH-NMR (CDCl3): 9.877 (s, IH), 7.813-7.833 (d, 2H, J=8 Hz), 6.984-7.004 (d, 2H, J=8 Hz), 3.882-3.899 (d, 2H, J= 6.8 Hz), 1.259-1.295 (m, IH), 0.669-.687 (m, 2H), 0.383 (bs, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Bromomethyl)cyclopropane, its application will become more common.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; SARMA, Pakala, Kumara Savithru; ACHARYA, Vinod, Parameshwaran; KASIBHATLA, Srinivas, Rao; VISWANADHAN, Vellarkad, Narayana; SHEKHAR, Polisetti; BISCHOFF, Alexander; WO2010/127212; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary