Tag: M.W=200-300

392662-65-6, Adding some certain compound to certain chemical reactions, such as: 392662-65-6, name is 3,6-Dibromothieno[3,2-b]thiophene, 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 392662-65-6.

Preparation of [(S)-1-((S)-2-{4-[4-(6-bromo-thieno[3,2-b]thiophen-3-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester A155. To a degassed mixture of 3,6-dibromo-thieno[3,2-b]thiophene (0.335 mmol), compound 8 (0.335 mmol), and sodium carbonate (1.34 mmol) in a mixture of DMF and water (10 mL/1 mL) was added Pd(PPh3)4 (0.335 mmol). The reaction mixture was heated for 1 hr at 80 C. Ethyl acetate and water were then added and the mixture was vigorously stirred for 10 min. The layers were partitioned into a phase separator. The organic layer was separated, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent: DCM to DCM/MeOH 9/1) to give compound A155 as a green gum in 74% yield. 1H NMR (DMSO-d6, 400 MHz) delta (ppm) 0.85 (d, J=6.61 Hz, 3H), 0.90 (d, J=6.61 Hz, 3H), 1.92-2.19 (m, 5H), 3.53 (s, 3H), 3.77-3.84 (m, 2H), 4.06 (t, J=8.34 Hz, 1H), 5.07-5.09 (m, 1H), 7.28 (d, J=8.32 Hz, 1H), 7.54 (d, J=1.97 Hz, 1H), 7.70-7.76 (m, 2H), 7.84-7.93 (m, 3H), 8.08-8.14 (m, 1H), 11.81 (s, 1H); MS (ESI, EI+) m/z=587-589 (MH+).

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 392662-65-6.

Reference:
Patent; IDENIX PHARMACEUTICALS, INC.; US2012/252721; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

174508-31-7, Name is 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine, 174508-31-7, 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.

4 Benzenamine, N, N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) (1) (0.419 g, 1.1 mmol), 2,5-Dibromo-3,4-ethylenedioxythiophene(0.2999 g,1 mmol), were dissolved in 30 ml DMF. a solution of K2CO3 (2 M, 10 ml) and two drops of aliquat 336 solution were added and degassed under argon for 30 min then Tetrakis(triphenyl-phosphine)palladium(0) (0.034 g, 0.03 mmol) added to the solution. The reaction mixture was stirred at 90 C for 24 h and quenched by adding water. The resulting mixture was extracted with methylene chloride.The combined organic layers dried over Na2SO4, and filtered. After removing the solvent, a yellow solid was obtained, which was purifiedby silica gel chromatography by using chloroform as eluent to give the title compound as a yellow solid. Yield (43%). FT-IR (cm-1): 1587(C = C aromatic), 1272 (C-N aromatic amine), 726 (C-Br)1H NMR(500 MHz, DMSO-d6, delta): 7.53-7.47 (m, 2H), 7.31-7.20 (m, 6H), 7.11-7.04 (m, 4H), 7.00 (m, 2H), 4.29 (s, 4H). MS: m/z (C24H18BrNO2S)found=463.02 (calcd. 464.37 For [M+]) with an error of DeltaM = 0.7963 ppm.

Statistics shows that 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine is playing an increasingly important role. we look forward to future research findings about 174508-31-7.

Reference:
Article; Abdellah, Islam M.; Koraiem, Ahmed I.; El-Shafei, Ahmed; Dyes and Pigments; vol. 164; (2019); p. 244 – 256;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 50548-45-3, name is 1-Bromodibenzo[b,d]furan, 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. 50548-45-3

20 g (80 mmol) of dibenzofuran-1-boronic acid, 2,06 g (40,1 mmol) of iodine, 3.13 g (17,8 mmol) of iodic acid, 80 ml of acetic acid, 5 ml of sulfuric acid, 5 ml of water and 2 ml of chloroform are stirred at 65 during 3 hours. After cooling, the mixture is mixed with water, the precipitated solid is removed, and the residue is washed three times with water. The residue is recrystallized from toluene and dichloromethane/heptane. (0151) The yield is 25.6 g (68 mmol), corresponding to 85% of theory.

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 50548-45-3.

Reference:
Patent; MERCK PATENT GMBH; PARHAM, Amir, Hossain; GROSSMANN, Tobias; KROEBER, Jonas, Valentin; (98 pag.)WO2017/71791; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 627871-16-3 name is 5-Bromo-4-fluoro-2-methylaniline, 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. 627871-16-3

[0008931 To a stirred solution of compound 3 (5.5 g, 1 eq) in DCM (50 mL), acetic anhydride (3.8 mL, 1.5 eq), and TEA (8.9 mL, 2.4 eq) was added and stirred under nitrogen atmosphere at room temperature for 1 8h. The reaction mixture was evaporated under reduced pressure. Residue was diluted with methanol and potassium carbonate was added, reaction was stirred at rt for 1 h. The reaction mixture was evaporated under reduced pressure and diluted with water, precipitate solid was filtered and dried to afford title compound. LCMS (mlz): 247.15 (M + 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-4-fluoro-2-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

393-36-2, Name is 4-Bromo-3-(trifluoromethyl)aniline, 393-36-2, 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.

4-Bromo-3-(trifluoromethyl)aniline was converted to 4-bromo-3-(trifluoromethyl)phenyl isocyanate according to Method B1.

Statistics shows that 4-Bromo-3-(trifluoromethyl)aniline is playing an increasingly important role. we look forward to future research findings about 393-36-2.

Reference:
Patent; BAYER CORPORATION; US2003/144278; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

67567-26-4, The chemical industry reduces the impact on the environment during synthesis 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, I believe this compound will play a more active role in future production and life.

Sodiumperborate tetrahydrate (18.5 g, 0.12 mol, 5.0 eq) was suspended in glacial acetic acid (125 mL) and heated to 65 C. 4-Bromo-2,6-difluoroanilline 2 (5.0 g, 24.0 mmol, 1.0 eq) dissolved in glacial acetic acid (50 mL) was added slowly through an funnel over 4 h. After the addition the reaction mixture was heated for 3 h additional hours before a second portion of NaBO3¡¤4H2O (6.0 g, 30.0 mmol) was added. Then the mixture was stirred for 14 h and a third portion of oxidating agent (9.0 g, 45.0 mmol) was added. 9 h after the third addition full consumption of the starting material was indicated by TLC. After cooling the mixture to room temperature, the formed solid was removed by filtration. The filtrate was poured into ice-cold water (300 mL). The precipitated solid was filtered off and dried to give the product as yellow solid (3.40 g, 60%). TLC [Silica, hexane/CHCl3 (5:1)]: Rf = 0.31. 1H NMR (300 MHz, CDCl3): delta = 7.36-7.28 (m, 2H). 13C NMR (75 MHz, CDCl3): delta = 154.7 (dd, J = 265.7, 2.8 Hz), 126.4 (t, J = 11.0 Hz), 117.2 (dd, J = 22.7, 3.9 Hz), [C-NO2 is not detected]. 19F NMR (282 MHz, CDCl3): delta = -117.0 (d, J = 7.1 Hz). LRMS (EI): m/z = 237 (calcd. 237 for C6H2 79BrF2NO2 [M]+).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2,6-difluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wagner, Sally; Scheunemann, Matthias; Dipper, Karolin; Egerland, Ute; Hoefgen, Norbert; Steinbach, Joerg; Brust, Peter; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 97 – 108;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1435-51-4 name is 1,3-Dibromo-5-fluorobenzene, 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. 1435-51-4

Preparation 37 1,3-Dibromo-5-methoxybenzene Sodium methoxide (8.80 ml of a 4.5M solution in methanol, 41.0 mmol) was added dropwise to a stirred solution of 3,5-dibromofluorobenzene (5.00 g, 19.0 mmol) in N,N-dimethylformamide (95 ml) at 0 C. under nitrogen. The reaction was allowed to warm to room temperature, stirred for 1 hour and then concentrated under reduced pressure. The residue was dissolved in ether and the resulting solution was washed with water (3*300 ml) and brine (300 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to provide the title compound (5.13 g) as a white solid. 1H-NMR (300 MHz, CDCl3): delta=3.79 (S, 3H), 7.00 (s, 2H), 7.26 (s, 1H).

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

Reference:
Patent; Jones, Lyn Howard; Mowbray, Charles Eric; Price, David Anthony; Selby, Matthew Duncan; Stupple, Paul Anthony; US2003/100554; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

627871-16-3, Adding a certain compound to certain chemical reactions, such as: 627871-16-3, name is 5-Bromo-4-fluoro-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 627871-16-3.

Step P5.1 : 1-Bromo-2-fluoro-4-methyl-5-(2,2,2-trichloro-ethyl)-benzeneTo a solution of vinylidene chloride (127 ml), tert-butyl nitrite (19 ml) and copper(ll)chloride (18.4 g) in acetonitrile (150 ml) was added a solution of 5-bromo-4-fluoro-2-methyl- phenylamine (Bioorganic & Medicinal Chemistry Letters (2006), 16(2), 457-460) (21.5 g) in acetonitrile (100 ml) dropwise below 200C. The reaction mixture was stirred at room temperature for 48 hours, poured on diluted HCI and extracted with tert-butyl methyl ether(3x). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 1 :4). Yield: 29.20 g of 1-bromo-2-fluoro-4-methyl-5-(2,2,2-trichloro- ethyl)-benzene as an oil.1H-NMR (CDCI3): delta 2.42 (s, 3H), 3.93 (s, 2H), 7.00 (d, 3J(H,F)=9.2Hz, 1 H), 7.69 (d,4J(H,F)=7.0Hz, 1 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, 5-Bromo-4-fluoro-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2009/49851; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1559-88-2, The chemical industry reduces the impact on the environment during synthesis 1559-88-2, name is 3-Bromo-1,2,4,5-tetrafluorobenzene, I believe this compound will play a more active role in future production and life.

The yield of 2,3,5,6-tetrafluorophenyl magnesium bromide measured in the same manner as Example 1 was 85.2 mol % based on 1-bromo-2,3,5,6-tetrafluorobenzene.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-1,2,4,5-tetrafluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nippon Shokubai Co., Ltd.; US6235222; (2001); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, 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. 28342-75-8

General procedure: E1 (3.00 equivalents), E2 (1 .00 equivalents) and E3 (1 .00 equivalents) were dissolved in dry DMF, NaH (6.00 equivalents) was added and the reaction mixture was stirred at 50 ¡ãC over night. Subsequently, NaH (3.00 equivalents) was added to the reaction mixture. The reaction mixture was poured on water and extracted repeatedly with dichloromethane. The combined organic layer was dried over sodium sulfate (Na2S04). The solvents were evaporated under reduced pressure to obtain Z1. Z1 (1 .00 equivalents) was dissolved in tert-butylbenzene and the solution was cooled to -30 ¡ãC. tert-Butyllithium (‘BuLi) (4.00 equivalents) was added dropwise and the reaction mixture was slowly heated up to 0 ¡ãC. After stirring for 30 minutes at 0 ¡ãC, the reaction mixture was cooled again to -30 ¡ãC. (0229) A solution of boron tribromide (BBr3, 2.2 equivalents) was added dropwise, the bath was removed and the reaction mixture was allowed to warm to room temperature (RT). Subsequently, the reaction mixture was heated at reflux at 120 ¡ãC for 5h. Volatiles were removed under reduced pressure to obtain Z3. (0230) A solution of Grignard compound/compounds [R1MgBr (1 .5 equivalents) / R2MgBr (1.5 equivalents)] was added dropwise to Z3 over a period of 30 min. After stirring for 1 h, MeOH was added to the reaction mixture and the solvents were evaporated under reduced pressure. The residue was dissolved in toluene and filtered with a pad of silica gel (toluene was used as eluent). The solvent was removed under reduced pressure. The crude product was dissolved in a minimum amount of toluene and then a small amount of heptane was added. The resulting precipitate was filtered to obtain P1 as a solid product.

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 28342-75-8.

Reference:
Patent; CYNORA GMBH; SEIFERMANN, Stefan; (41 pag.)WO2019/52940; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary