Month: June 2021

Electric Literature of 626-88-0, The chemical industry reduces the impact on the environment during synthesis 626-88-0, name is 1-Bromo-4-methylpentane, I believe this compound will play a more active role in future production and life.

[008191 Prepared using General Procedure 12: To a stirred solution of tert-butyl (8)-i – (2-(5-Qert-butyl)thiophene-2-carboxamido)-3-(4-(5-(4-hydroxyphenyl)pyrimidin-2- yl)phenyl)propanoyl)azetidine-3-carboxylate (INT-48) (300 mg, 0.479 mmol) in DMF (5mL) was added Cs-CO3 (197 mg, 0.58 mrnol) and 1-bromo-4-methylpentane (158 mg, 0.96 mmol). The reaction mixture was stirred for 18 h at 65C then diluted with aq. NaHCO3 (100 ml, saturated) and extracted with EA (2 X 100 mL). The combined organic layers were dried (Na2SO4), concentrated, and purified by column chromatography (EA/ hexane)to afford 188 mg (54%) of tert-butyl (S-1-(2-(5-(tert- butyl)thiophene-2-carboxarnido)-3-(4-(5 -(4-((4-methylpentyl) oxy)phenyl)pyrimidin-2- yl)phenyl)propanoyl)azetidine-3 -carboxylate .LCMS-ESI (m/z) calculated for C42H52N4O5S 724.96; found 725.3 [M±H] , /p. = 12.71 mm (Method 16). ?H NMR (400 MHz, CDC13) oe 8.97 (d, J = 7.5 Hz, 2H). 8.45 (d, J = 5.5 Hz, 2H), 7.55 (s, 2H). 7.49 – 7.31 (rn. 3H), 7.05 (d, J 6.6 Hz, 2H), 6.82 (s, IH), 6.68 (d, J= 28.8 Hz, 1H), 4.82 (s, 1H). 4.30 (s. 0.5H). 4.07 (rn, 5.5H), 3.56 (s, 0.5H), 3.31 – 3.09 (rn, 2H), 2.91 (s, 0.5H),1.83 (s, 2H), 1.60 (d, J= 25.3 Hz, 1H), 1.40 (s, 16H), 1.29 (s, 4H), 0.95 (s, 6H).

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, 1-Bromo-4-methylpentane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CELGENE INTERNATIONAL II SARL; BOEHM, Marcus, F.; MARTINBOROUGH, Esther; MOORJANI, Manisha; TAMIYA, Junko; HUANG, Liming; YEAGER, Adam, R.; BRAHMACHARY, Enugurthi; FOWLER, Thomas; NOVAK, Andrew; MEGHANI, Premji; KNAGGS, Michael; GLYNN, Daniel; MILLS, Mark; (851 pag.)WO2016/94729; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 327-52-6, 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. 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Example 1 Preparation of (3S)-methyl 3-(tert-butoxycarbonylamino)-4-hydroxy-4-(2,4,5-trifluorophenyl)butyrate 13.2 g metal magnesium and 400 ml tetrahydrofuran were added into a clean flask. 116.05 g trifluorobromobenzene was added thereto dropwisely after initiation by iodine and the reaction was kept at 30-40 C. for 3 hours for use. 29.9 g (S)-methyl 3-(tert-butoxycarbonyl amino)-4-oxo-n-butyrate was dissolved in 300 ml THF, and cooled to -20 C. The solution mentioned above was added thereto dropwisely over two hours and kept at the temperature for 3 hours. 400 ml ammonium chloride solution was added dropwisely. Layers were separated. The aqueous layer was extracted with tetrahydrofuran. The organic layer was dried and concentrated to get 14.5 g (3S)-methyl 3-(tert-butoxy carbonylamino)-4-hydroxy-4-(2,4,5-trifluoromethyl-phenyl)butyrate (yield: 66%).

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

Reference:
Patent; Zhu, Guoliang; Zhang, Jian; Yang, Lljun; Yao, Qingdan; Ying, Jie; US2012/178957; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 57946-63-1, 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 57946-63-1 as follows.

Commercially available 2-bromo-4-(trifluoromethyl)benzeneamine (2.06 g, 8.6 mmol) was suspended in concentrated HCl (4.0 mL). Clumps of material were broken up with a spatula, then ice (-2.6 g) was added to the mixture and it was cooled over an ice bath. A solution of NaNO2 (0.64 g, 9.3 mmol) in H2O (2.6 mL) was added dropwise while maintaining the temperature of the reaction mixture at 0-50C. The mixture was stirred for 20 minutes over the ice bath, then poured slowly into a solution of KI (12.5 g, 75.3 mmol) in H2O (16 mL). The BCI mixture was stirred for several minutes, then left to settle over night. EPO The reaction mixture was extracted thrice with hexanes. The combined organics were washed twice with IM NaOH, once with aqueous sodium bisulfite solution, then with brine. The solution was dried over MgSO4, vacuum filtered through Celite.(R). and cone in vacuo to give 2.33 g of 2-bromo-4-(trifluoromethyl)-iodobenzene. By TLC (100percent hexanes) and 1H NMR analysis, it was determined that the product was of sufficient purity to be used in the subsequent step. The resultant diethyl [2-bromo-4-(trifluoromethyl)- phenyljdifluoromethylphosphonate was synthesized from 2-bromo-4-(trifluoromethyl)- iodobenzene according to Example 25 except that chlorotrimethylsilane (several drops) was used in place of acetic acid. Compound 86 was synthesized according to procedures similar to those of Example 40 from this corresponding diethyl phosphonate. MS (ES-):m/z 352.9, 354.9 (M – H). 1H NMR: (DMSO-d6, 400 MHz) delta 8.07 (s, IH), 7.89 (d, J = 8.0, IH), 7.78 (d, J = 8.0, IH).

According to the analysis of related databases, 57946-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CEPTYR, INC.; WO2006/55525; (2006); 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. 67344-77-8, name is 1-(3-Bromophenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

Step 1 : N-(3-Bromobenzyl)-N-methylacetamideTo a DMF (0.1 M) solution of 3-bromo-N-methylbenzylamine (1 eq.), Hunig’s base (3 eq) and 4-(dimethylamino)pyridine (5percent loading) was added acetyl chloride (1.5 eq). The resulting reaction mixture was stirred at RT for 16 h. After quenching the reaction with sat. aq. NaHCO3, the mixture was extracted with EtOAc. The organic extract was washed with 10percent aq. HCl, sat. aq. NaHCO3, and brine. Drying over Na2SO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a yellow oil. Purification by way of flash chromatography (SiO2, 4: 1 (v/v) Hex : EtOAc -> EtOAc) afforded the title compound as a yellow oil.

The synthetic route of 67344-77-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2007/9250; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1575-37-7,Some common heterocyclic compound, 1575-37-7, name is 4-Bromobenzene-1,2-diamine, molecular formula is C6H7BrN2, 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.

Preparation 1 5-Bromo-benzo[1,2,5]thiadiazole To 4-bromo-benzene-1,2-diamine (17 g, 91 mmol) was added thionyl chloride (200 ml). One drop of DMF was added to the reaction mixture. The reaction mixture was heated at reflux under argon at 80 C. overnight. The reaction mixture was cooled to room temperature and added portionwise to ice in a large beaker and neutralised with solid sodium bicarbonate. The mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was collected and dried (MgSO4). The solvent was removed under reduced pressure. The title compound was isolated by column chromatography on silica gel eluding with 90% ethyl acetate/10% methanol. (12 g, 62%); 1H NMR (250 MHz, CDCl3) delta: 7.61 (1H, dd, J=9, 2 Hz), 7.82 (1H, d, J=9 Hz), 8.16 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromobenzene-1,2-diamine, its application will become more common.

Reference:
Patent; Gaster, Laramie Mary; Harling, John David; Heer, Jag Paul; Heightman, Thomas Daniel; Payne, Andrew Hele; US2004/152738; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 13633-25-5, 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. 13633-25-5 name is 1-Bromo-4-phenylbutane, 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.

Step 1. In a 250 ml three-necked flask, 1 g of a catalyst P-W2CNC, 1-bromo-4-phenylbutane 8.0 g, DMF 50 ml, and mechanical stirring were sequentially added.Put 1.8 g of methylparaben, K2CO 33.6 g, and heat to 115 C.Reaction 11h;Step 2: After the reaction is cooled to room temperature, the K2CO3 solid is removed by suction filtration.Add 50 ml of water to the filtrate, turbid, stir for 10 min, add about 3 mol / L of HCl solution to adjust pH = 2;Step 3. Extract the above system with dichloromethane, wash with ionized water,The solvent dichloromethane was removed by rotary evaporation to give an orange liquid;Step 4, the orange liquid is placed in a single-mouth bottle, 3.0 g of NaOH, 50 ml of water and 40 ml of ethanol are added, and the mixture is refluxed for 3 hours in an oil bath, and the ethanol is distilled off.The residue was adjusted to pH=2 with 3 mol/L of HCl;Step 5, after extracting the above system with dichloromethane, the organic phase is steamed.A sticky yellow solid was obtained, and after adding an appropriate amount of isopropanol, the mixture was stirred, solid crystallized, and suction filtered to give white crystals of 4-(4-phenylbutoxy)benzoic acid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-phenylbutane, and friends who are interested can also refer to it.

Reference:
Patent; Yang Cheng Feiyang; Yang Chengfeiyang; Chen Huaqi; (7 pag.)CN108689843; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 345965-54-0, name is 1-(4-Bromophenyl)cyclopropanamine, 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 345965-54-0, Application In Synthesis of 1-(4-Bromophenyl)cyclopropanamine

[1-(4-Bromophenyl)-cyclopropyl]-dipropylamine (Intermediate 121) To a solution of 1-(4-bromophenyl)-cyclopropylamine (Intermediate 116) in CH3CN/HOAc (5 mL, 9:1, v/v) and THF 3 mL at 0 C. was added propionaldehyde (277.0 mg, 4.95 mmols) and NaCNBH3 (153.0 mg, 2.47 mmols). The reaction was warmed to room temperature and after 5 hours quenched with H2O. The pH of the solution was adjusted to 8-9 using aqueous NaOH and extracted with EtOAc. The combined extracts were washed with H2O and saturated aqueous NaCl, dried (MgSO4) and concentrated under reduced pressure. The title compound, 190.0 mg (56%), was isolated by column chromatography (2-5% EtOAc-hexanes). 1H NMR (CDCl3) delta: 7.42 (2H, d, J=8.3 Hz), 7.18 (2H, d, J=8.3 Hz), 2.39 (4H, t, J=7.3 Hz), 1.62-1.40 (4H, m), 0.96 (2H, m), 0.86 (6H, t, J=7.3 Hz), 0.80 (2H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Bromophenyl)cyclopropanamine, and friends who are interested can also refer to it.

Reference:
Patent; Allergan Sales, Inc.; US6313107; (2001); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

348-57-2, name is 1-Bromo-2,4-difluorobenzene, 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. category: bromides-buliding-blocks

1-Bromo-2,4-difluoro-5-nitrobenzene To a stirred solution of 1-bromo-2,4-difluorobenzene (0.512 g, 2.65 mmol, Aldrich, used as received) in conc. H2 SO4 (5.0 mL) at 0° C., KNO3 (0.275 g, 2.72 mmol) was added in one portion. The resulting solution was allowed to warm to 28° C. and was stirred at that temperature overnight. It was then poured into ice (50 g) and extracted with ethylacetate (50 mL). The extract was dried over Na2 SO4, and evaporated to afford 0.576 g (91percent) pure title compound as light red oil; 1 H NMR (CDCl3); delta7.141 (dd, 1H, J1 10.2 Hz, J2 =7.8 Hz), 8.375 (t, 1H, J=7.5 Hz).

The synthetic route of 348-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The State of Oregon, acting by and through The Oregon State Board of Higher Education, acting for and on behalf of The Oregon Health Sciences University; The University of Oregon; The Regents of the University of California; US5514680; (1996); A;,
Bromide – Wikipedia,
bromide – Wiktionary

58971-11-2, name is 3-Bromophenethylamine, 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. HPLC of Formula: C8H10BrN

Step 2: N-[2-(3-bromophenyl)ethyl]-2,2,2-trifluoroacetamide To a solution of 2-(3-bromophenyl)ethanamine (28.1 mmol) in DMC (100 mL) was added 2,6-lutidine (29 mmol). The reaction mixture was cooled to 0 C. and then TFAA (28.1 mmol) was slowly added. The reaction mixture was allowed to stir and warm to rt overnight. Water (90 mL) was added and the organic solution was separated. The aqueous solution was extracted with DCM. The organic solutions were combined, washed with 1N HCl and aq. Sat. NaHCO3, dried over Na2SO4, filtered and concentrated to give N-[2-(3-bromophenyl)ethyl]-2,2,2-trifluoroacetamide (25.1 mmol, 89%) as a white solid which was used without further purification.

The synthetic route of 58971-11-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/171754; (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. 1753-75-9, name is 5-Bromobenzo[c][1,2,5]thiadiazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H3BrN2S

Synthesis of 5,5′-bis(2,1,3-benzothiadiazole) A reaction mixture prepared by adding 4.6 g (21.4 mmol) of 5-bromo-2,1,3-benzothiadiazole and 2 g (31.5 mmol) of copper powder to 10 mL of dimethylformamide was heated with stirring at 150 C. for 6 hours. This reaction mixture was cooled and then poured into water (40 mL), and a resulting precipitate was filtered and collected. After this precipitate was dried, it was extracted with benzene (20 mL*3). After combining these benzene extracts, the combined extract was dried under vacuum to complete dryness. A resulting oily residue was triturated with petroleum ether, and a mother liquor was removed to yield 2.1 g of 5,5′-bis(2,1,3-benzothiadiazole) (melting point, 61 to 62 C.; yield, 73%).

According to the analysis of related databases, 1753-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHOWA DENKO K. K.; US2009/149676; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary