Tag: M.W=100-200

1003-98-1,Some common heterocyclic compound, 1003-98-1, name is 2-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.

Compound 15 (67.5 g, 0.355 mol) was added to the 300 mL 15 % aq. HCl. A resulting suspension was stirred for 1 h at 80 oC, then cooled to -5 C and NaNO2 (26.0 g, 0.365 mol) in H2O (50 mL) was slowly added. The mixture was stirred for 1.5 h at -5 C and then the excess of HNO2 was neutralized with urea. The solution of KI (57.2 g, 0.0355 mol) in 50 mL H2O was added dropwise at 0 oC (caution, the fast evolution of N2 was observed). The mixture was warmed to room temperature and stirred for 40 h. After this time CHCl3 was added, water phase was extracted with CHCl3 (3 ¡Á 100 mL), joined organic phases were washed with saturated solution of NaHCO3 (200 mL), 5% solution of Na2S2O3 (200mL) and5% solution of Na2S2O5 (200mL). Organic phase was dried over MgSO4 and concentrated under reduced pressure. The obtained crude product was distilled under reduced pressure (b.p. 90-91 oC, 2 Tr) affording 17 as viscous oil (69.1 g, 64%). 1H NMR (400 MHz, CDCl3): delta 7.79 (ddd, J = 9.0, 5.8, 0.9 Hz, 1H), 7.38 (ddd, J = 8.3, 2.9, 0.8 Hz, 1H), 6.78 (ddd, J = 9.0, 7.9, 2.9 Hz, 1H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1003-98-1, its application will become more common.

Reference:
Article; Durka, Krzysztof; Laudy, Agnieszka E.; Charzewski, ?ukasz; Urban, Mateusz; St?pie?, Karolina; Tyski, Stefan; Krzy?ko, Krystiana A.; Luli?ski, Sergiusz; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 11 – 24;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 1575-37-7, name is 4-Bromobenzene-1,2-diamine, 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 1575-37-7. 1575-37-7

A 250 mL four-necked flask equipped with a mechanical stirrer, thermometer, reflux condenser, nitrogen inlet and bubble counterEach o-diaminobenzene (0.031 mol) (Formula 1a) was added dropwise to glacial acetic acid (50 mL) under a nitrogen atmosphere.The resulting slurry was cooled to 4 [deg.] C in an ice-bath. Sodium nitrite in water (6 mL) (2.24 g,0.032 mol) in THF Was added dropwise over 40 minutes while maintaining the temperature of the reaction mixture below & lt; RTI ID = 0.0 & gt; 10 C. & lt; / RTI & gt; GeneratedThe slurry was allowed to warm to room temperature and analyzed using a KI / amylose test paper until analysis for free HNO2 was negative and starting material was not visible in thin layer chromatography (16 h)Under stirring. The resulting slurry was filtered; the solid residue washed with water (100 mL) and the resulting solid was further purified by recrystallization from ethanol (20 mL). The product was dried for 24 h at 50 C. and 5 mbar and obtained as off-white solid. Yield: 67%.

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 4-Bromobenzene-1,2-diamine.

Reference:
Patent; BASF SE; Reihard, Robert; Kalor, Martin; Router, Michael; Li, Yuchuo; Cliff, Andreas; (31 pag.)KR2016/30566; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

3814-30-0, name is (Bromomethyl)cyclopentane, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 3814-30-0

EXAMPLE 2 Preparation of 1-(cyclopentylmethyl)imidazole A solution of sodium ethoxide was made by dissolving sodium (2.3 g, 0.1 mole) in absolute ethanol (100 ml). Imidazole (6.8 g, 0.1 mole) was then added. The mixture was heated under reflux and cyclopentylmethylbromide (16.3 g, 0.1 mole) was added dropwise. The reaction mixture was allowed to reflux for a further 16 hours after addition. The mixture was then left to cool. The solid material was then filtered off and the filtrate evaporated down under vacuum. The residue was taken up in 2 N HCl (150 ml) and washed with ether (50 ml). The solution was basified with excess 10 N NaOH and the product extracted with chloroform (3*50 ml). Combined extracts were dried over anhydrous MgSO4 and chloroform removed under vacuum to give yellowish oil. The crude product was purified on a silica gel column eluted with EtOAc/MeOH (9:1). The product fractions were combined and evaporated down under vacuum to leave 1.9 g of slightly yellowish oil. This was distilled under vacuum. B.pt. 68-69 C./0.125 mmHg. Yield 0.95 g.

Statistics shows that 3814-30-0 is playing an increasingly important role. we look forward to future research findings about (Bromomethyl)cyclopentane.

Reference:
Patent; Burroughs Wellcome Co.; US4284641; (1981); A;,
Bromide – Wikipedia,
bromide – Wiktionary

55289-36-6, These common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, 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.

Reference Production Example 8 (0631) A mixture of 25.0 g of 1-bromo-2-methyl-3-aminobenzene, 60.0 g of triphosgene, and 400 ml of toluene was stirred with heating under reflux for 3 hours. The reaction mixture allowed to cool was concentrated under reduced pressure to obtain 30.3 g of 1-bromo-3-isocyanato-2-methylbenzene (referred to as 8A). (0632) 1H-NMR (CDCl3) delta(ppm): 2.42 (3H, s), 7.00 (1H, dt, J=0.5, 8.0 Hz), 7.05 (1H, dd, J=1.7, 8.0 Hz), 7.39 (1H, dd, 1.5, 7.7 Hz).

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; SUMITOMO CHEMICAL COMPANY, LIMITED; SHIODA, Takayuki; ARIMORI, Sadayuki; (149 pag.)US2016/159755; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 586-61-8 as follows. 586-61-8

To fuming nitric acid (5 mL) cooled to 5 was added neat 4-bromoisopropylbenzene(1.0 g, 5.023 mmol) dropwise at such a rate that the reaction temperature remained below 10. The reaction was stirred for 2 hours at 5-10, quenched with ice (50 g), extracted with ethyl acetate (50 mL), and the organic extract was washed with water (2×25 mL) and brine (25 mL), then dried over magnesium sulfate. filtered and concentrated by rotary evaporation. The residue was purified by silica gel flash chromatography eluting with 5:95 ethyl acetate/hexanes to afford the title compound as a light yellow solid (1.03 g, 4.22 mmol, 84%). 1H NMR (300 MHz, CHLOROFORM-D) delta ppml.27 (d, J=6.99 Hz, 6 H) 2.75 – 3.23 (m, 1 H) 7.29 (dd, J=8.82, 2.21 Hz, 1 H) 7.63 (d, J=8.09 Hz, 1 H) 7.69 (d, J=2.21 Hz, 1 H); MS (DCI) m/z 261/263 (M+NH4)+.

According to the analysis of related databases, 586-61-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/133753; (2008); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 583-70-0, name is 2,4-Dimethylbromobenzene, molecular formula is C8H9Br, 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. 583-70-0

General procedure: Magnesium turnings (180 mg, 7.5 mmol) and a little iodine were placed in a 50 mL three-necked flask equipped with a magnetic stirring bar, a reflux condenser and a nitrogen bubbling tube flushed with nitrogen. Then, RBr (5 mmol) was added dropwise to react with magnesium in dry THF (15 mL) for 1 h at 45 C. Selenium powder (0.4 g, 5 mmol) was added to the reacting mixture in batches. After reacting for 0.5 h, CuI (142 mg, 15 mol%), L-proline(180 mg, 30 mol%), toluene (20 mL), H2O (5 mL) and styrene (5 mmol) were added and kept for 8 h at 85 C. After cooled at room temperature, the cool mixture was added with dilute hydrochloride aqueous solution, and then filtered. The filtrate and filtered residue were both extracted with ethyl acetate. After the ethyl acetate was evaporated under reduced pressure, the crude product was analyzed by GC-MS directly. Isolated yields and pure samples subjected to spectroscopic analysis were obtained by TLC with n-hexane as developing solvent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 583-70-0, its application will become more common.

Reference:
Article; Gao, Fei; Tang, Yu; Li, Zhi-Hao; Pan, Feng; Yang, Jun; Zhang, Yuan-Ming; Tetrahedron Letters; vol. 53; 42; (2012); p. 5688 – 5690;,
Bromide – Wikipedia,
bromide – Wiktionary

A common compound: 1647-26-3, name is 1-Bromo-2-cyclohexylethane, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1647-26-3

1-(5-thiazolyl)-3-cyclohexylpropan-1-ol A solution of thiazole-5-carboxaldehyde (2.31 g, 20.4 mmol) in 20 mL of in THF was added to a cold (0 C.) solution of 2-cyclohexylethylmagnesium bromide (prepared from 2-bromoethylcyclohexane (7.88 g) and magnesium turnings (1.22 g)) in 30 mL of ethyl ether and the mixture stirred 30 minutes. The cold bath was removed and the mixture stirred for 2 hours more and then quenched by the addition of 3N aqueous HCl. The solution was stirred until 2 clear phases resulted and then the layers were separated. The pH of the aqueous phase was adjusted to 4 with 2M aqueous sodium carbonate and then extracted with 3 portions of ethyl acetate. All the organic phases were combined and washed with brine, dried, filtered and concentrated. The residue was purified by column chromatography on silica gel (125 g, 50% ethyl acetate/hexanes) to provide 2.69 g (58%) of the title compound. MS (DCI, NH3): 226 (MH+); 243 (M+NH4)+.

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, 1647-26-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; University of Pittsburgh; US6204293; (2001); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 7745-91-7, name is 3-Bromo-4-methylaniline, 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. 7745-91-7

4-(4,4?-Dimethoxybenzhydryl)-thiophenyl boronic acid (10 mmol) and 3-bromo-4-methylaniline (1.86 g, 10 mmol) were dissolved in MeCN (40 mL). Pd (PPh3)4 (50 mg) and aqueous solution K2CO3 (1M, 22 mL) were added before the reaction mixture was heated portion-wise in a microwave oven (160 C., 400 sec). Products were distributed between ethyl acetate and water. The organic layer was washed with water, brine and dried over MgSO4. Evaporation yielded an oil that was used without purification in the next step. ESI-MS ink calc. 441.0. found 442.1 (M+1).

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 7745-91-7.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 7745-91-7, name is 3-Bromo-4-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 7745-91-7

Step 1.2: N-(3-Bromo-4-methyl-phenyl)-3-trifluoromethyl-benzamide A solution of 5.8 mL (39 mmol) 3-trifluoromethyl-benzoyl chloride in 80 mL acetonitrile is treated drop-wise and at RT with 12.2 mL (78 mmol) triethylamine, followed by 7.8 g (42.9 mmol) 3-bromo-4-methyl-aniline. During the slow addition of the 3-trifluoromethyl-aniline, the temperature rises to about 30 C. The mixture is stirred at room temperature for 10 h and then cooled to 0 C. Water is added (100 mL) and the resulting precipitate filtered off, washed with water and dried. The solid is suspended in hexane stirred for a few min, filtered and dried again to give the title compound as a colourless solid; m.p. 153-155 C.; HPLC tR=4.54 min.

The synthetic route of 7745-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Caravatti, Giorgio; Furet, Pascal; Imbach, Patricia; Martiny-Baron, Georg; Perez, Lawrence Blas; Sheng, Tao; US2006/35897; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

55289-36-6, Adding a certain compound to certain chemical reactions, such as: 55289-36-6, name is 3-Bromo-2-methylaniline, 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 55289-36-6.

The mixture of 25.0g of 1-bromo-2-methyl-3-amino benzene and 60.0g of triphosgene 400mL of toluene was heated under reflux for 3 hours with stirring. The cooled reaction mixture was concentrated under reduced pressure to give 30.3g of 1-bromo-3-methyl-2-phenyl isocyanate.

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-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Chemical Co., Ltd.; Hou, Zenghua; Gao, Quiaohuangshu; (253 pag.)CN105408322; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary