Tag: M.W=200-300

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. 29086-41-7, name is 1,1-Bis(bromomethyl)cyclopropane, A new synthetic method of this compound is introduced below., Product Details of 29086-41-7

Example 1271: 5-(5-Chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)- spiro[2,3]hexane-5-carboxylic acidStep lEthyl 5-(5-chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)- spiro[2,3]hexane-5-carboxylateEthyl 2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)acetate (0.6 g, 1.36 mmol) was dissolved in anhydrous DMF (3OmL), NaH (60% wt. in paraffin oil, 0.136 g, 3.4 mmol) was added at 00C. The reaction mixture was stirred for 30 min at room temperature and l,l-bis(bromomethyl)cyclopropane (0.482 g, 1.4 mmol, for preparation see J. Org. Chem 1993, 58, 4122-26) was added drop wise at 0 0C. The reaction mixture was stirred an additional Ih at 0 0C and saturated NH4CI solution (1OmL) was added. The reaction mixture was extracted with EtOAc (3x20mL) and the combined organic phases were washed with water (3x20mL) and brine (2OmL), and dried over MgSO4. The volatiles were removed under reduced pressure and the residue was purified by flash column chromatography to yield compound ethyl 5-(5-chloro-6-(2,2,2- trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)- spiro[2,3]hexane-5-carboxylate (150 mg) as a low melting solid.

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; ENVIVO PHARMACEUTICALS, INC.; WO2009/86277; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 68322-84-9, These common heterocyclic compound, 68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, 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 product from Scheme 14, Step 4 (136 mg, 0.407 mmol, 1 eq), 2-bromo-1- fluoro-4-(trifluoromethyl)benzene (148 mg, 0.61 mmol, 1.5 eq), CuI (16 mg, 0.084 mmol, 0.2 eq), and Cs2CO3 (265 mg, 0.82 mmol, 2 eq) were combined in DMF (1.5 ml_) and heated for 3h at 900C. The reaction was filtered and the filtrate was partitioned between EtOAc and water. The aqueous layer was discarded, and the organic layer was washed three times more with water, was dried over anhydrous sodium sulfate, was filtered, and was evaporated to afford a crude residue. Preparative thin layer silica gel chromatography (20cmX20cm, 1000 mum, developed with 3% EtOAc in hexanes) afforded the desired product (145 mg).

Statistics shows that 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene is playing an increasingly important role. we look forward to future research findings about 68322-84-9.

Reference:
Patent; SCHERING CORPORATION; WO2009/140342; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 327-75-3,Some common heterocyclic compound, 327-75-3, name is 1-Bromo-2,4-bis(trifluoromethyl)benzene, molecular formula is C8H3BrF6, 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.

To a stirred solution of 4-nitro-lH-pyrazole (2.0 g, 6.51 mmol, 1 eq) in DMF (20ml) was added K CO portion wise at 0 C and stirred for 10 minutes. l-(bromomethyl)-2,4- bis(trifluoromethyl)benzene (0.73 gm, 6.51 mmol, 1 eq) was added drop wise 0 C. The reaction mixture was allowed to stir for 1 hour at RT. Product formation was confirmed by LCMS. After completion of reaction, reaction mixture was diluted with water and extracted with ethyl acetate (100 mL X 3). Combined organic extracts were washed with water (100 mL x 4), dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain 1- (2,4-bis (trifluoromethyl) benzyl)-4-nitro-lH-pyrazole (2.1 g, as white solid). LCMS: 326 [M+H]+.

The synthetic route of 327-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRAXIS BIOTECH LLC; ALFARO, Jennifer; BELMAR, Sebastian; NUNEZ VASQUEZ, Gonzalo Esteban; PUJALA, Brahmam; SATHE, Balaji Dashrath; BERNALES, Sebastian; CHAKRAVARTY, Sarvajit; THAKRAL, Pooja; PATIDAR, Rajesh Kumar; (344 pag.)WO2019/195810; (2019); A2;,
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. 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, A new synthetic method of this compound is introduced below., Formula: C6H4BrF2N

Preparation example 5: Preparation of (Z)-N’-(4-bromo-2,6-difluorophenyl)-N-isopropyl acetamidine 4-bromo-2,6-difluroaniline (7.87 g, 37.9 mmol)), N-isopropylacetamide (7.65 g, 75.7 mmol) and triethylamine (5.7 g, 56.9 mmol) were dissolved in toluene (150 mL), and phosphorus oxychloride (5.8 g, 37.9 mmol) was added slowly. After the addition, the mixture was heated to reflux for 3 h. Then, the reaction mixture was cooled to room temperature, the solvent was removed by reduced pressure distillation, and dichloromethane (200 mL) was added. The resultant mixture was washed with saturated sodium hydrogen carbonate solution (2×100 mL) twice, dried by anhydrous sodium sulfate, filtrated under suction, and distilled under reduced pressure, to get the solid title compound (7.3 g, yield: 66.2%).

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; Xuanzhu Pharma Co., Ltd.; WU, Frank; CHEN, Bo; (105 pag.)EP3091008; (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 327-51-5 as follows. SDS of cas: 327-51-5

To a Et2O solution (200 mL) containing 1,4-dibromo-2,5-difluorobenzene (19.72 g, 72.5 mmol) cooled to -78 degrees C. was added 30.5 mL of a 2.5 M hexanes solution of n-BuLi (76.2 mmol). The resulting green solution was stirred for 20 min at -78 degrees C. when DMF (7.95 g, 10.8 mmol) was added. The reaction was stirred for 30 min and then quenched with H2O. The organics were taken up in EtOAc and washed with sat. NaHSO4 followed by drying over MgSO4. The solvent was removed in vacuo and the residual oil purified on the Biotage (2-5% EtOAc/hexanes) yielding 11.4 g (51.7 mmol) of 4-bromo-2,5-difluorobenzaldehyde. 1H NMR (400 MHz, CDCl3) delta 10.2 (s, 1H), 7.57 (m, 1H), 7.45 (m, 1H) ppm.

According to the analysis of related databases, 327-51-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, molecular formula is C7H7BrFN, 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. SDS of cas: 112734-22-2

(2) To a solution of 4-bromo-2-fluorobenzylamine (0.93 g) and triethylamine (1.3 ml) in N,N-dimethylformamide (5 ml) was added a solution of ethyl(R)-2,5-dioxo-3-(2-trichloroacetylpyrrol-1-yl)pyrrolidine-3-carboxylate (1.16 g) in N,N-dimethylformamide (3 ml) dropwise at room temperature. This mixture was stirred at room temperature for 8 hours. This reaction mixture was diluted with ethyl acetate, then washed with 1 M hydrochloric acid (three times), water (four times), and saturated brine successively, dried over magnesium sulfate, filtered and concentrated to give a crude product as yellow oil. This was purified by flash column chromatography (n-hexane: ethyl acetate =2:1) to give(3R)-2′-(4-bromo-2-fluorobenzyl)spiro[pyrrolidine-3,4′(1’H)-pyrrolo[1,2-a]pyrazine]-1′,2,3′,5(2H’)-tetraone (831 mg, 65%). This product was further crystallized from n-hexane-ethyl acetate to give the desired product (385 mg) as crystal.Mp: 189-191 C. 1H NMR (400 MHz, DMSO-d6, 22 C.) delta: 12.2 (br s, 1H), 7.73 (dd, 1H, J=2.0, 3.2 Hz), 7.55 (dd, 1H, J=2.0, 9.6 Hz), 7.36 (dd, 1H, J=2.0, 8.4 Hz), 7.17-7.12 (m, 2H), 6.53 (dd, 1H, J =2.8, 4.0 Hz), 5.04 (d, 1H, J=15.2 Hz), 4.96 (d, 1H, J=15.6 Hz), 3.57 (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 112734-22-2, its application will become more common.

Reference:
Patent; Tanaka, Daisuke; Tanaka, Hiroaki; US2011/190497; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 73918-56-6, The chemical industry reduces the impact on the environment during synthesis 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, I believe this compound will play a more active role in future production and life.

Step 1 A solution of 4-bromophenethylamine (10 g, 50 mmol), di-tert-butyldicarbonate (21.82 g, 100 mmol), triethylamine (13.9 ml, 100 mmol), and anhydrous methanol (350 ml) was refluxed for 2 h. The reaction mixture was concentrated in vacuo and the residue was stirred with water, filtered, washed with water and air dried to give N-(tert-butoxycarbonyl)-4-bromophenethylamine (15 g).

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, 2-(4-Bromophenyl)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Syntex (U.S.A.) LLC; US6323223; (2001); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 328-70-1, name is 1-Bromo-3,5-bis(trifluoromethyl)benzene, molecular formula is C8H3BrF6, 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. Computed Properties of C8H3BrF6

EXAMPLE 3 1-(3,5-Bis(trifluoromethyl)phenyl)ethan-1-one A solution of 3,5-Bis(trifluoromethyl)bromobenzene (29.3 g) in 30 mL of THF was added to a mixture of magnesium granules (5.10 g) in THF (200 mL) heated at reflux (the reaction was initiated with approximately 5 mL of the bromide solution; the remainder was added slowly over 1 h). The mixture was aged for 30 min at reflux, cooled to RT and added over 1 h to a solution of acetic anhydride (40 mL) in THF (40 mL) maintained at -15 C. The resulting dark brown mixture was warmed to 10 C. in a water bath, and water (300 mL) was added. The pH of the vigorously stirred biphasic mixture was adjusted to 8.0 using 50% NaOH. MTBE (300 mL) was added, the layers were separated and the aqueous layer was further extracted with MTBE (3*150 mL). The organic layers were combined and concentrated in vacuo (bath at 30-35 C.; 50-80 torr). The concentrate was then distilled at atmospheric pressure to provide the pure product (20.7 g; 82% yield) with a boiling point of 187-189 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 328-70-1, its application will become more common.

Reference:
Patent; McNamara, James M.; Zhao, Matthew M.; US2002/22725; (2002); A1;; ; Patent; Brands, Karel M. Jos; Tsay, Fuh-Rong; Conrad, Karen M.; Zhao, Matthew M.; US2002/52494; (2002); 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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

Example 7; Preparation of Compound of Formula IVThe compound of formula X (50 g), HOBt (26.5 g)/EDCI (37.5 g) and DMF (500 mL) were loaded into a reactor at 25+/-5 C. After being reacted for 3 h, the compound of formula II (39 g) was added to the reactor. The reaction mixture was stirred at 80 C. for about 18 hours while monitoring for the consumption of active ester by HPLC. After being cooled to 25+/-5 C., the mixture was dropped to a solution of half-saturated aqueous solution of sodium hydrogen carbonate, and the product was precipitated as canary yellow solid.The yield of this step was about 29.0% by weight. The purity of the isolated product was 95% (% on area by HPLC method described in Appendix 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 54962-75-3.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; US2010/16590; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 129316-09-2, 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. 129316-09-2 name is 1,3-Dibromo-5-(tert-butyl)benzene, 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: [00826] Synthesised according to general procedures GP1 1 – from i) 1 ,3-dibromo-5-(fe/f- butyl)benzene (2.0 g, 6.85 mmol), ‘BuLi (1 .6 M in pentane; 8.5 ml_, 13.6 mmol), THF (70 mL and 5 ml_), dimethyl disulfide (0.74 mL, 8.22 mmol); -78 C?rt; chromatography (EtOAc/cyclohexane 0?10%), 1 .50 g, 85%. ii) (3-bromo-5-(te/ -butyl)phenyl)(methyl)sulfane (1 .50 g, 5.79 mmol), m-CPBA (77%; 2.50 g, 1 1 .1 mmol), DCM (50 mL); rt, 12 h; chromatography (EtOAc/cyclohexane 0?30%), 1 .40 g, 83%. NMR (500 MHz, CDCI3) delta 7.87 (t, J = 1 .6 Hz, 1 H), 7.85 (t, J = 1 .6 Hz, 1 H), 7.76 (t, J = 1 .7 Hz, 1 H), 3.05 (s, 3H), 1 .32 (s, 9H). General procedures GP11 (1119) [00687] ‘BuLi was added dropwise over 20 min to a solution of 1 ,3-dibromo-5-(fe/?-butyl)benzene in THF at -78 C and stirring was maintained at -78 C for 10 min. A solution of disulfide (RSSR) in THF was added dropwise over 20 min at the same temperature and the reaction was warmed slowly to rt. Sat. NH4CI was added. The aqueous phase was extracted with EtOAc (3 x). The combined organic phase was dried over MgSC , filtered and the solvent was removed under reduced pressured. The crude was purified by chromatography (1120) [00688] m-CPBA was added in small portions to a solution of the intermediate sulfide in DCM. The mixture was stirred at rt for 12 h and diluted with EtOAc. The solution was washed with sat. NaHCC (3 x), dried over MgSC , filtered and the solvent was subsequently removed under reduced pressure. The crude was purified by chromatography

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-(tert-butyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; SPRINGER, Caroline; MARAIS, Richard; NICULESCU-DUVAZ, Dan; LEUNG, Leo; SMITHEN, Deborah; CALLENS, Cedric; TANG, Haoran; (403 pag.)WO2017/141049; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary