Category: bromides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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 22385-77-9, Formula: C14H21Br

General procedure: To a mixture of Pd(OAc)2 (23 mg, 0.1 mmol), DPE-Phos (125 mg,0.2 mmol), and Cs2CO3 (652 mg, 2.0 mmol) was added a solutionof 4a (496 mg, 1.0 mmol) and 2-bromo-1,3,5-trimethylbenzene(300 mg, 1.5 mmol) in 1,4-dioxane (15 mL) under N2, and the reactionmixture was heated at 110 °C for 17 h with stirring. After coolingto r.t., and removal of solvents, the mixture was extracted withCH2Cl2 (3 × 20 mL), and the combined organic extracts werewashed with brine (20 mL) and dried (Na2SO4). Purification of theresidual oil by column chromatography on silica gel (hexanes?EtOAc, 10:1) afforded 5a

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-3,5-di-tert-butylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhu, Shifa; Wang, Chao; Zhao, Songxian; Xiao, Yelin; Hu, Lang; Huang, Zhipeng; Synthesis; vol. 46; 2; (2014); p. 212 – 224;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 112734-22-2, These common heterocyclic compound, 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, 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.

Step c) 2-[(4-Bromo-2-fluorophenyl)methyl]-1,2,3,4-tetrahydro-1,3-dioxo-4-isoquino-linecarboxylic Acid Methyl Ester To a solution of 3-methoxy-1-oxo-1H-2-benzopyran-4-carboxylic acid methyl ester (5.0 g, 21.37 mmol) in DMF (100 mL) were added 4-bromo-2-fluorobenzylamine (4.36 g, 21.37 mmol) and Et3 N (5.96 mL, 42.74 mmol). The mixture was stirred at 80 C. for 30 minutes, poured into H2 O (1500 mL), acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and crystallization from acetone/hexane (after cooling to -20 C.) gave a white solid (7.6 g, 87.7%, m.p. 149-150 C.). 1 H NMR (DMSO-d6, 400 MHz): delta [3.67 (s), 4.0 (s), 3H, –CO2 Me, tautomeric], [5.06 (q), J=15.4 Hz, 5.30 (s), 2H, –NCH2 –, tautomeric], 5.4 (s), 1H, CH–CO2 Me, tautomeric], 7.07-8.43 (m, 7H, Ar–H, tautomeric) IR (KBr, cm-1): 1670 (CO), 1605 (CO) MS (+FAB): 406 (80, M+ +H), 374 (470, M+ –OCH3) Anal. Calcd.: C, 53.22; H, 3.23; N, 3.45; Found: C, 53.19; H, 2.98; N, 3.40.

The synthetic route of 112734-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; US5102886; (1992); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 19190-91-1, name is 5,6-Dibromo-1,2-dihydroacenaphthylene, 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 19190-91-1, HPLC of Formula: C12H8Br2

General procedure: Dibromoarene 1 (0.5 mmol), alkyne 2 (0.6 mmol), Pd(OAc)2 (5 mol%, 5.6 mg ),Xantphos (5.5 mol%,16 mg), K2CO3 (1.5 mmol, 207 mg) were added into a Schlenkflask. The flask was evacuated and backfilled with nitrogen (3 cycles). Dry DMF (5mL) was added by syringe. The mixture was heated to 120 C and stirred until thereaction finished (TLC analysis). After cooling to room temperature, the mixture wasextracted three times with ethyl acetate. The organic layers were combined and driedover Na2SO4. After filtration, the solvents were evaporated. The crude product wasfurther purified by silica gel chromatography, using petroleum ether and ethyl acetateas eluents to provide the pure product

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:
Article; An, Wenbo; Li, Gaoqiang; Ma, Jun; Tian, Youping; Xu, Feng; Synlett; vol. 25; 11; (2014); p. 1585 – 1590;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 28342-75-8, 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. 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under a nitrogen atmosphere and at reflux temperature there was added 1,5-bromo-2,4-difluorobenzene (90.0 g), phenylboronic acid (which 88.6 g of), tripotassiumphosphate (154.0g), Pd-132 (Johnson Matthey (JohnsonMatthey)) (1.6g), toluene (900ml),isopropanol (300ml) and water (150ml) of the flask was heated for 1 hour. After stoppingthe reaction, the reaction solution was cooled until room temperature and water wasadded to carry out liquid separation. After the solvent was distilled off under reducedpressure, silica gel short column (eluent: heptane / toluene = 1/2 (volume ratio)) to bepurified, thereby obtaining 4 ‘, 6′-difluoro-1,1’: 3 ‘, 1’ – terphenyl (86.0g).

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, 1,5-Dibromo-2,4-difluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kwansei Gakuin School Corporation; Tian, Shanzuoci; Zhong, Zhongzongyiliang; Zhong, Daoguiyi; Ping, Jingdagui; Xiao, Yeyangping; Zhi, Lianyizhi; Ni, Jingping; Song, Xiawusi; Sheng, Tianlizhao; (405 pag.)CN105431439; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 203302-95-8,Some common heterocyclic compound, 203302-95-8, name is 4-Bromo-3,5-difluoroaniline, molecular formula is C6H4BrF2N, 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 solution of the 4-bromo-3,5-difluoroaniline (5 g, 20 mmol) in acetic acid (60 mL) was added NIS (5.68 g). The reaction mixture was stirred at room temperature for two hours, and poured into water (300 mL). The product was extracted with ethyl acetate (2*200 mL), and the combined organic layers were washed with 1 N aqueous NaOH (200 mL) and saturated aqueous sodium thiosulfate (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The oily residue was filtered through a plug of silica gel, eluting with heptane/ethyl acetate (4:1). The filtrate was concentrated in vacuo to give the title compound (7.34 g) as a white solid. 1H NMR (500 MHz, CDCl3) delta 6.44 (dd, J=10.00, 1.95 Hz, 1H) 4.46 (br. 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 4-Bromo-3,5-difluoroaniline, its application will become more common.

Reference:
Patent; PFIZER INC.; Bhattacharya, Samit; Cameron, Kimberly; Dowling, Matthew; Fernando, Dilinie; Ebner, David; Filipski, Kevin; Kung, Daniel; Lee, Esther; Smith, Aaron; Tu, Meihua; US2013/267493; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 766-46-1, name is 2′-Bromophenylacetylene, molecular formula is C8H5Br, 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. Formula: C8H5Br

[Example 2] The following will describe other synthetic examples based on reaction formula (VI) below. First, a method of synthesis from 1,4-bis[(2-bromophenyl)ethynyl]-2,5-dibromobenzene (6) as a raw material will be described. A 3/1 toluene/triethylamine (9 mL) solution of 2-bromo-1-ethynylbenzene (90 mg, 4.98 mmol) was added to a mixed 3/1 toluene/triethylamine (12 mL) solution of 1,4-dibromo-2,5-diiodobenzene (1.15 g, 2.35 mmol), dichlorobis(triphenylphosphine) palladium (II) (33 mg, 47 mmol), and copper iodide (18 mg, 95 mmol) at room temperature and stirred for 12 hours at room temperature. A 1N aqueous solution of hydrochloric acid was added to the reaction mixture. The mixture was then subjected to extraction using methylene chloride. The obtained organic layer was washed in a saturated saline solution and dried with anhydrous magnesium sulfate. After removing the drying agent by filtering, the filtered solution was concentrated under reduced pressure. The resultant mixture was recrystallized from benzene, to obtain 1.17 g (1.97 mmol) of the target product 6 in the form of a white solid at a yield of 84%. 1H NMR (CDCl3): delta 7.20-7.35 (m, 4H), 7.59-7.65 (m, 4H), 7.83 (s, 2H). 13C NMR (CDCl3): delta 90.81, 95.00, 123.57, 124.47, 125.59, 126.40, 127.02, 130.15, 132.54, 133.66, 136.34. Anal. Calcd for C22H10Br4: C, 44.49; H, 1.70. Found: C, 44.42; H, 1.54.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 766-46-1, its application will become more common.

Reference:
Patent; Japan Science and Technology Agency; EP1548019; (2005); 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. 1435-54-7, name is 1,3-Dibromo-2-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3Br2F

To 1 .00 g (3.94 mol) 1 ,3-dibromo-2-fluoro-benzene, 820 mg (3.94 mmol) N-phenyl-1 H- benzimidazol-2-amine and 2.51 g (1 1.8 mmol) potassium phosphate tribasic in 15 ml DMA are added, and it is stirred at 160 C for 15 h under nitrogen. The reaction mixture is poured on water. The product is filtered off and washed with water. Yield 1.38 g (96.5 %) 1H NMR (400 MHz, CDCI3): delta = 8.87 (d,1 H), 7.74-7.80 (m, 3H), 7.62-7.67 (m, 2H), 7.49-7.53 (m, 2H), 7.36-7.43 (m, 2H), 7.25-7.30 (m, 1 H), 7.18 (t, 1 H)

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 1435-54-7.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; SCHAeFER, Thomas; KAWAMURA, Masahiro; NAGASHIMA, Hideaki; (314 pag.)WO2017/56052; (2017); 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. 14659-58-6, name is 2-Bromo-5-fluoro-1,3-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

A solution of 2-bromo-5-fluoro-1,3-dimethylbenzene (25 g, 123 mmol) in tetrahydrofuran (300 mL) was cooled to -78 C and n-butyllithium (59.1 mL, 148 mmol) wasadded dropwise at a rate to keep the internal temperature at or below -75 C. The mixture was stirred for 2 hours and then trimethylborate (16.51 mL, 148 mmol) was added and the mixture stirred for 3 hours at -78 C, then warmed to ambient temperature. After 4 hours, the mixture was cooled to -10 C and a precooled solution of NaOH (7.39 g, 185 mmol) and 30 % hydrogen peroxide (201 mL, 1970 mmol) was added. Once the addition was completethe mixture was allowed to warm to ambient temperature overnight. The pH of the mixture was adjusted to pH 1 with 2M HC1. 400 mL of ethyl ether and 200 mL of water were added and the layers were separated. The aqueous layer was extracted with 3 x 200 mL of ether, and the combined organic layers were washed with saturated NaHCO3 and saturated Na5203, then stirred with a saturated aqueous Na5205 solution (200 mL) for 15 minutes. The organicphase was dried with anhydrous magnesium sulfate, filtered, and concentrated. The residues were taken up in 1/1 diethyl ether/pentane and flushed through a silica plug. Concentration of the filtrate provided 11 .47g (67%) of the title compound.

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 14659-58-6.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; HASVOLD, Lisa A.; LIU, Dachun; MCDANIEL, Keith F.; PRATT, John; SCHRIMPF, Michael; SHEPPARD, George S.; WANG, Le; LI, Bing; (191 pag.)WO2017/177955; (2017); A1;,
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. 52997-43-0, name is 7-(Bromomethyl)pentadecane, A new synthetic method of this compound is introduced below., Safety of 7-(Bromomethyl)pentadecane

General procedure: The general procedure for the alkylation of fluorene (C-alkylation) is as follows. A two-neck flask with a three-way stopcock and a rubber septum was charged with fluorene (4mmol, 0.664 g) and dry THF (20 mL). KOtBu (12mmol, 1.346 g) was added to the flask at room temperature, then the mixture was heated at reflux for 20min. The flask was allowed to reach room temperature with stirring for 30min. 1-Bromododecane (8.8mmol, 2.20 g) was slowly added to the reaction mixture at 0 C, then again the flask was allowed to reach room temperature with stirring for overnight. 2.2.1 The First Posttreatment: After checking TLC and the 1HNMR spectrum, the reaction mixture refluxed for one hour. The reaction was quenched by the addition of sat. NH4Cl aqueous solution, extracted into n-hexane (50 3 mL), was hed successively with water, brine, dried (anhydrous Na2SO4) and concentrated by rotary evaporator to afford the reaction mixture(including the target dialkylated fluorene and olefin.). 2.2.2 The Second Posttreatment: 2-(a): To a mixtureof the crude mixture of the first posttreatment, 5wt% Pd/C(0.100 g) and acetic acid (AcOH, 4mmol) in THF (10 mL) were slowly added portionwise NaBH4 (4mmol, 0.151 g), andthe resulting mixture was stirred at room temperature for 12 hours. Thereafter, the mixture was filtered and the precipitate was washed with hexane and concentrated by rotary evaporatorfor NMR measurement. 2-(b): Since the alkylation was an almost quantitative reaction, the expected amount of olefin in the mixture was equalto the excess amount of starting alkyl halide (0.8mmol in the above case). It could be assumed that 0.8 mmol of olefin should be treated with the small excess of 9-BBN (1.2mmol, 1.5 eqvs olefin). A two neck flask with a three-way stopcock and a rubber septum was charged with the above reaction mixture and dry THF (20 mL). 0.5M 9-BBN in THF (1.2mmol, 2.4mL) was added to the flask at 0 C and then the flask was allowed to warm to room temperature and stirred for one hour. To quench the remaining 9-BBN in the reaction, aminoalcohol (2-dimethylaminoethanol, 0.5mmol, 0.045 g) was added to the flask and stirred for another hour. 39 The final reaction mixture was quenched by the addition of water (5 mL), extracted into EtOAc (50 3 mL), washed successively with water, brine, dried (anhydrous Na2SO4) and concentrated by rotary evaporator to afford the crude mixture. 2.2.3 The Third Posttreatment: The crude product was purified on short silica-gel [5 cm (diameter of column) 10 cm (length of deposition of silica-gel) was enough for this scale] with n-hexane as eluent to give the dialkylated fluorene.

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:
Article; Okamoto, Ken; Lu, Fengniu; Nakanishi, Takashi; Bulletin of the Chemical Society of Japan; vol. 91; 8; (2018); p. 1258 – 1263;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 4549-33-1, A common heterocyclic compound, 4549-33-1, name is 1,9-Dibromononane, molecular formula is C9H18Br2, 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.

Synthesis of Compound 9.1 [0189] To a solution of 2075-45-8 (1.30 g, 8.84 mmol, 1.0 eq) in CH3CN (20 ml) were added K2C03 (1.41 g, 13.26 mmol, 1.5 eq) and 4549-33-1 (5.05 g, 7.68 mmol, 2.0 eq). The reaction mixture was stirred at 65 C for 16 h. After cooling down to ambient temperature, the resulting solution was diluted with H20 (100 mL), extracted with ethyl acetate (100 ml). The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by silica gel column (PE / EA = 10 / 1) to give 9.1 (2.08 g, yield: 66%) as a white solid. 1H NMR (400 MHz, CDC13) delta: 7.44 (s, 1H), 7.38 (s, 1H), 4.09 (t, J = 1.2 Hz, 2H), 3.41 (t, J = 1.2 Hz, 2H), 1.87-1.80 (m, 4H), 1.42-1.37 (m, 2H), 1.29-1.24 (m, 8H); ESI-MS (M+H) +: 351.0.

The synthetic route of 4549-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN IDEC MA INC.; JENKINS, Tracy; VESSELS, Jeffery; WO2014/143672; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary