Month: November 2020

Some common heterocyclic compound, 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrF4, 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. 40161-54-4

INTERMEDIATE 7 MC181 Y4-[2-Bromo-5-(trifluoromethyl)phenoxy]cvclohexanolTo a solution of 4-bromo-3-fluorobenzotrifluoride (2 g, 8.23 mmol) and a mixture of cis and trans cyclohexane-l,4-diol (3.82 g, 32.9 mmol) in DMF (41.2 ml) was added NaH 5 (0.658 g, 16.46 mmol) at 0 C. The reaction mixture was warmed to room temperature then heated at 80 0C for 2 h. The mixture was poured onto IN HCl (100 mL) and extracted with EtOAc (3×25 mL). The combined organic fractions were washed with water (50 mL) then dried over Na2SO4. Purification by Combiflash chromatography (SiO2-40 g, gradient elution of 10- 50% EtOAc/hexanes over 25 min) afforded the title product as a 7:3 mixture of isomers. 10 Major isomer: 1H NMR (500 MHz, acetone-d6): delta 7.82 (dd, IH), 7.43 (d, IH), 7.23 (d, IH), 4.76-4.70 (m, IH), 3.84-3.76 (m, IH), 3.67 (d, IH), 2.18-2.12 (m, IH), 2.06-1.95 (m, IH), 1.82-1.71 (m, 2H), 1.69-1.60 (m, 2H), 1.55-1.47 (m, 2H). MS: m/z 339, 341 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40161-54-4, its application will become more common.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2008/128335; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

The chemical industry reduces the impact on the environment during synthesis 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, I believe this compound will play a more active role in future production and life. 142808-15-9

At -78 C., 181.07 ml of a 2.5M (452.7 mmol) solution of n-butyllithium were added dropwise to a solution of 63.9 g (452.7 mmol) of 2,2,6,6-tetramethylpiperidine in 833 ml of dry THF. The mixture was stirred at this temperature for 30 min. 100.0 g (411.5 mmol) of 4-bromo-2-fluoro-1-(trifluoromethyl)benzene were then added dropwise at -78 C. The mixture was stirred at this temperature for 2 h. 33.1 g (452.7 mmol) of DMF were then added dropwise at -78 C. The reaction mixture was then stirred for 2 h. For work-up, 300 ml of water were added to the contents. The mixture was extracted three times with in each case 200 ml of dichloromethane. The combined organic phases were washed with 300 ml of 1M hydrochloric acid and then with 300 ml of a saturated aqueous sodium chloride solution. The organic phase was dried and the filtrate was freed of the solvent. 96.2 g of the desired product were obtained.

The chemical industry reduces the impact on the environment during synthesis 142808-15-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; AHRENS, Hartmut; TIEBES, Joerg; WALDRAFF, Christian; DIETRICH, Hansjoerg; SCHMUTZLER, Dirk; GATZWEILER, Elmar; ROSINGER, Christopher; (33 pag.)US2017/107183; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

39478-78-9, 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. 39478-78-9, name is 5-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5-Bromo-2-methylphenol; A solution of concentrated sulphuric acid (6 mL) in distilled water (75 mL) was added to 5-bromo-2-methylaniline (1 g, 5.38 mmol). The resultant suspension was heated to 90 C. and stirred for 4.5 h. The reaction mixture was then cooled using an ice bath and a solution of sodium nitrite (384 mg, 5.57 mmol) in water (5 mL) was added to the reaction mixture at 0 C. The reaction was then allowed to warm to ambient temperature. The reaction mixture was then added to a solution of concentrated sulphuric acid (6 mL) in water (75 mL) which had been preheated to 90 C. The reaction mixture was stirred for 1 h at 90 C. and allowed to cool, on standing, overnight. A precipitate was observed in the reaction mixture. The precipitate was collected by filtration, washed with water, and dried in a vacuum oven to afford 5-bromo-2-methylphenol as a brown solid (510 mg, 2.73 mmol, 51%). M.S. (ESI) (m/z) 185, 187[M-H]-

The synthetic route of 39478-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. Organon; US2007/185156; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

22385-77-9, 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. 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, This compound has unique chemical properties. The synthetic route is as follows.

2-methyl-4-methoxy-7-(3,5-Di-tert-butylphenyl)-1H-indene To a solution of 3,5-di-tert-butylphenylmagnesium bromide obtained from 59.3 g (0.220 mol) of 1-bromo-3,5-di-tert-butylbenzene and 7.60 g (0.313 mol, 1.42 eqv.) of magnesium turnings in 450 ml of THF 1.00 g (1.28 mmol, 0.65 mol. percent) NiCl2(PPh3)IPr and a solution of 53.4 g (0.197 mol) of 2-methyl-4-bromo-1,7-dimethoxyindane in 50 ml of THF were added. A vigorous reflux occurs approximately after ca. 30 sec and ceased after the following 30 sec. This mixture was stirred for 30 min at room temperature. Finally, 1000 ml of water and then 50 ml of 12 M HCl were added. The product was extracted with 500 ml of dichloromethane, organic layer was separated, the aqueous layer was additionally extracted with 200 ml of dichloromethane. The combined organic extract was dried over K2CO3, passed through a short column with silica gel 60 (40-63 mum), and then evaporated to dryness. To the residue dissolved in 700 ml of toluene 1.4 g of TsOH was added. This solution was refluxed using Dean-Stark head for 20 min, cooled to room temperature, washed with 200 ml of 10percent aqueous NaHCO3. The organic layer was separated, the aqueous layer was extracted with 2*100 ml of dichloromethane. The combined organic solution was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: hexane-dichloromethane=10:1, then 1:1, vol.). This procedure gave 67.6 g (99percent) of 2-methyl-4-methoxy-7-(3,5-di-tert-butylphenyl)-1H-indene as a yellowish crystalline powder. The latter can be recrystallized from n-hexane with marginal loss of weight. Anal. calc. for C25H32O: C, 86.15; H, 9.25. Found: C, 86.09; H, 9.23. 1H NMR (CDCl3): delta 7.40 (m, 1H, 4-H in tBu2C6H3), 7.35 (m, 2H, 2,6-H in tBu2C6H3), 7.15 (d, J=8.4 Hz, 1H, 6-H in indenyl), 6.88 (d, J=8.4 Hz, 1H, 5-H in indenyl), 6.70 (m, 1H, 3-H in indenyl), 3.92 (s, 3H, OMe), 3.41 (m, 2H, 2,2′-H in indenyl), 2.15 (s, 3H, 2-Me in indenyl), 1.38 (s, 18H, tBu).

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; BOREALIS AG; RESCONI, Luigi; CASTRO, Pascal; VIRKKUNEN, Ville; IZMER, Vyatcheslav V.; KONONOVICH, Dmitry S.; KULYABIN, Pavel Sergeevich; VOSKOBOYNIKOV, Alexander Z.; US2015/344596; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

A common compound: 3638-73-1, name is 2,5-Dibromoaniline, 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. 3638-73-1

General procedure: To a mixture of 2-naphthol (1 mmol), aniline derivatives(1 mmol) and Kojic aldehyde (1 mmol) was added nanoFe3O4(at)SiO2-boric acid (15 mg). The mixture was stirredat 40 C under solvent free condition in an oil bath and thecompletion of reaction was monitored by TLC (EtOAc / nhexane:1:4). After completion of the reaction, the mixturewas cooled to room temperature, ethanol (2 mL) was added,and themixture was stirred for 10 min. The catalyst was separatedout using an external magnet and the obtained solid wascollected by filtration and purified by recrystallization from(EtOH/acetone, 4:1) or was subjected to silica gel preparativelayer chromatography (EtOAc/n-hexane, 1:5) to give pyran asa pure solid. The recovered catalyst was washed with EtOH,dried and reused for the next run. The catalyst was recoveredand reused for five times without any significant changes inthe yield and the reaction time.

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, 3638-73-1, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Teimuri-Mofrad, Reza; Gholamhosseini-Nazari, Mahdi; Esmati, Somayeh; Shahrisa, Aziz; Journal of Chemical Sciences; vol. 129; 9; (2017); p. 1449 – 1459;,
Bromide – Wikipedia,
bromide – Wiktionary

1435-51-4, 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 1435-51-4 as follows.

step 1-A solution of 57a, sodium methoxide (1 equivalent) and DMF were stirred overnight under an N2 atmosphere at RT. The volatile solvents were removed in vacuo and the residue partitioned between Et2O and water. The organic phase was washed with 5% NaOH, water and brine, dried (MgSO4), filtered and evaporated to afford 57b.

According to the analysis of related databases, 1,3-Dibromo-5-fluorobenzene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Roche Palo Alto LLC; US2006/25462; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

The chemical industry reduces the impact on the environment during synthesis 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, I believe this compound will play a more active role in future production and life. 38573-88-5

Preparation 8; TERT-BUTYL S-^1S-DIFLUOROPHENYL)-S-HYDROXYAZETIDINE-I – CARBOXYLATE; To a solution of 3-bromo-1 ,2-difluorobenzene (2.3 g, 11.8 mmol) in dry diethylether (20 ml) at -78¡ãC, under nitrogen was added n-butyllithium (2.5 M in hexane, 4.7 ml, 11.8 mmol) dropwise. The mixture was stirred for 1 h after which a solution of 1-Boc-3-azetidinone (2.0 g, 11.7 mmol) in dry diethyl ether (20 mL) was added dropwise. The resulting mixture was stirred at -78¡ãC for 15 min and then brought to ambient temperature and stirred for 2 h. Aqueous ammonium chloride (50 mL, 50percent) and diethylether was added, the organic phase was collected and the aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane 1 :4 to 1 : 1 ) to give the title compound (1.9 g). MS m/z (rel. intensity, 70 eV) 285 (M+, 1 ), 156 (55), 141 (69), 127 (bp), 57 (88).

The chemical industry reduces the impact on the environment during synthesis 38573-88-5. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NSAB, FILIAL AF NEUROSEARCH SWEDEN AB, SVERIGE; SONESSON, Clas; SWANSON, Lars; PETTERSSON, Fredrik; WO2010/58017; (2010); 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. 937046-98-5 name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, 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. 937046-98-5

Compound 1414To 7-bromo-pyrrolo[2,l -f][1,2,4]ti-iazin-4-ylaiTiine (0.501 g) and THF (31.5 mL) was added 1,2-bis(chloromethylsilyl)ethane (0.518 g). To the cloudy solution was added NaH (60% in mineral oil, 0.235 g). After 10 minutes the solution was cooled in a -40 C bath and nBuLi (2.16 M in hexanes, 3.6 mL) was added. After 13 min the lactone (1.031 g) was added in THF (3 mL) followed by a wash with 0.1 mL of THF. After 3h the reaction mixture was at -20 C and was quenched with saturated NH4CI (3 mL) followed by the addition of water (7 mL). The solution was left to warm to room temperature overnight. The next day EtOAc (32 mL) was added and after separating the organics they were washed with water and brine (10 mL each). The organics were dried over Na2S04, filtered, concentrated and the resulting residue purified by column chromatography on silica gel giving 0.567 g (48%) of the tri- prenyl protected lactol 14, (M H)/Z

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; GILEAD SCIENCES, INC.; BUTLER, Thomas; CHO, Aesop; GRAETZ, Benjamin, R.; KIM, Choung, U.; METOBO, Samuel, E.; SAUNDERS, Oliver, L.; WALTMAN, Andrew, W.; XU, Jie; ZHANG, Lijun; WO2011/35250; (2011); 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. 50548-45-3 name is 1-Bromodibenzo[b,d]furan, 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. 50548-45-3

5 grams (g) of 1-bromodibenzo[b,d]furan (Intermediate (a)), 6.4 g of 9,9-dimethyl-9H-fluoren-2-amine (Intermediate (b)), 6.4 g of potassium tert-butoxide (KtOBu), 0.3 g of P(tBu)3, and 0.4 g of Pd2 (dba)3 were diluted in toluene, followed by stirring at a temperature of 100 C. under reflux. After a 20-hour lapse, the temperature was lowered to room temperature. Subsequently, the reaction was terminated utilizing water. An organic layer was extracted therefrom three times utilizing ethyl acetate. Then, the organic layer was dried utilizing anhydrous magnesium sulfate, followed by filtration under reduced pressure. The obtained residue was separated and purified through column chromatography to thereby obtain 6.5 g of Intermediate 1-1 (yield: 86%). The compound thus obtained was identified by liquid chromatography-mass spectrometry (LC-MS). C27H21NO: calc’d: M+375.16 foun’d: 375.26

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromodibenzo[b,d]furan, and friends who are interested can also refer to it.

Reference:
Patent; Samsung Display Co., Ltd.; KIM, Jongwoo; BAEK, Jangyeol; JEONG, Eunjae; HAN, Sanghyun; KIM, Youngkook; HWANG, Seokhwan; US2019/185460; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1003-98-1, 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. 1003-98-1, name is 2-Bromo-4-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 5 2-(2-amino-5-fluorophenyl)-3-methyl-2-cyclopenten-1-one 4.46 g (21.44 mmol) of 2-bromo-4-fluoroaniline, 3.30 g (23.582 mmol) of 5-methyl-1-cyclopenten-2-one boronic acid compound, 0.204 g (0.177 mmol) of tetrakis(triphenylphosphine)palladium, and 3.41 g (32.173 mmol) of sodium carbonate were loaded to 250 mL schlenk flask, and then 66 mL of degassing DME and 22 mL of H2O that had been purged with N2 were added thereto using a syringe. The mixture was reacted at 90 C. for 12 hours. The work-up was the same as in Example 3 (3.76 g, 79%). 1H NMR (CDCl3): =6.74(td, J=8.8 Hz, 1H, Ph), 6.45 (d, J=7.6 Hz, 1H, Ph), 3.65 (br s, 2H, NH2), 2.71-2.69 (m, 2H, CH2Cp), 2.54-2.52 (m, 2H, CH2CP), 2.07 (s, 3H, CH3); 13C {1H} NMR (CDCl3): =207.05, 176.05, 155.17(d, J=12.9 Hz, Ph), 152.63 (dd, J=12.9 Hz, Ph), 150.11 (d, J=12.9 Hz, Ph), 137.79, 129.60(d, J=3.1 Hz, Ph), 120.43 (dd, J=12.9 Hz, Ph), 111.97 (dd, 1.8 Hz, 22 Hz, Ph), 103.00 (t, 22 Hz, Ph), 34.66, 32.28, 18.50

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; LG Chem, Ltd.; US7538239; (2009); B2;,
Bromide – Wikipedia,
bromide – Wiktionary