Tag: M.W=300-400

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. 558-13-4, name is Carbontetrabromide, A new synthetic method of this compound is introduced below., Application In Synthesis of Carbontetrabromide

b 3-(Fluoro)phenethyl bromide To a solution of 3-(fluoro)phenethyl alcohol (3.8 g, 27.0 mmol), in anhydrous dichloromethane (100 ml), cooled to 0 C., was added carbon tetrabromide (11.25 g, 34.0 mmol) and triphenylphosphine (10.62 g, 41.0 mmol). After stirring for 0.5 h the solvent was removed in vacuo and diethyl ether (100 ml) was added to the residue. The resultant precipitate was removed by filtration, the filtrate evaporated under reduced pressure and the crude product chromatographed on silica-gel eluding with ethyl acetate/hexane (1:1) to give 3-(fluoro)phenethyl bromide (5.51 g, 100%), delta (250 MHz, CDCl3) 3.16 (2H, t, J=7.4 Hz, CH2), 3.57 (2H, t, J=7.4 Hz, CH2), 6.91-7.01 (3H, m, Ar–H), 7.24-7.33 (1H, m, Ar–H).

The synthetic route of 558-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme, Ltd.; US5889008; (1999); A;,
Bromide – Wikipedia,
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Some common heterocyclic compound, 827-08-7, name is 1,2-Dibromo-3,4,5,6-tetrafluorobenzene, molecular formula is C6Br2F4, 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. Product Details of 827-08-7

Butyllithium (1.6 M in hexanes, 12.6 mL, 20.16 mmol) was added dropwise to a stirred solution of 1,2-dibromotetrafluorobenzene (2.6 g, 8.44 mmol) in ether (50 mL) at -78 C. After 2 hours this solution was slowly added to a pre-cooled solution (-78 C.) of trimethylborate (2.3 mL, 20.52 mmol) in ether (25 mL). The resulting suspension was stirred at -78 C. for two hours then gradually warmed to room temperature and hydrolyzed with 20 mL of 10% HCl. The yellow organic phase was separated and the aqueous phase was extracted with dichloromethane (3*15 mL). The combined organic phases were washed with water (3*10 mL) and dried over magnesium sulfate. Removal of solvent under reduced pressure gave a yellow oil that was recrystallized from water at a pH of 4 to afford a crystalline solid. (1.5 g, 75%) 19F NMR (D2O/HCl) delta: -136.6 (d, JF-F=28.3 Hz, 2F, C6F4), -156.5 (d, JF-F=28.3 Hz, 2F, C6F4). 11B NMR (D2O/HCl) delta: 16.9 (br).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 827-08-7, its application will become more common.

Reference:
Patent; Piers, Warren Edward; Chase, Preston A.; Henderson, Lee Douglas; US2005/222463; (2005); A1;,
Bromide – Wikipedia,
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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. 626-39-1, name is 1,3,5-Tribromobenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 626-39-1

n-Butyllithium (2.5 mL of a 2.5 mol/l solution in n-hexane,6.3 mmol) was added to a solution of 1,3,5-tribromobenzene (7) (2.00 g, 6.35 mmol) in Et2O (40mL) at -78 C under inert atmosphere. After 10 min, CuCN (282 mg, 3.18 mmol) was added andthe reaction mixture was allowed to warm up to -60 C within 90 min. Nitrobenzene (0.98 mL,9.53 mmol) was then added in one portion and the dark solution stirred while warming toambient temperature (16 h). An aqueous solution of NH3 (12.5% w/w, 80 mL) was slowly addedand the resulting mixture was extracted with MTBE (3 x 50 mL). The combined organic layerswere washed with water (50 mL) and brine (50 mL), dried over MgSO4, filtered and the solventwas removed in vacuum. Further purification was accomplished by column chromatography(SiO2, n-hexane, Rf 0.69). The resulting material was washed with acetone (20 mL) to give theproduct 8 as a colorless solid (722 mg, 1.54 mmol, 48%), mp 190 C (ref.22 190-191 C). 1HNMR (500 MHz, CDCl3): delta 7.70 (t, J 1.7 Hz, 2 H), 7.59 (d, J 1.7 Hz, 4 H) ppm. 13C{1H} NMR(126 MHz, CDCl3): delta 141.8 (2 C), 133.9 (2 CH), 129.0 (4 CH), 123.6 (4 C) ppm. IR (ATR):3103 (w), 3068 (m), 1579 (m), 1541 (s), 1407 (m), 1387 (m), 1098 (m), 1068 (m), 847 (s), 752(s), 672 (m), 653 (m) cm-1. MS (EI, 70 eV), m/z (%): 466 (95) [M+], 308 (25), 150 (25), 84(100). Anal. calcd. for C12H6Br4 (469.80): C 30.68, H 1.29; found C 30.68, H 1.30.

According to the analysis of related databases, 626-39-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Behler, Florian; Wickleder, Mathias S.; Christoffers, Jens; ARKIVOC; vol. 2015; 2; (2014); p. 64 – 75;,
Bromide – Wikipedia,
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Related Products of 3344-70-5,Some common heterocyclic compound, 3344-70-5, name is 1,12-Dibromododecane, molecular formula is C12H24Br2, 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.

1.0 g of compound 3,2.63 g of 1,12-dibromododecane,0.43 g of potassium hydroxide and 0.16 g of tetrabutylammonium bromide,Was added to a mixture of 10 ml of dichloromethane and 6.5 ml of water,The mixture was stirred at room temperature under nitrogen for 24 hours,With 30 millilitersWashed twice with water, washed once with 15 ml of saturated brine, the organic layer was separated, dried over anhydrous sodium sulfate,The solvent was removed on a rotary evaporator and purified by chromatography on a 200-300 mesh silica gel column (eluent ethyl acetate / petroleum ether volume ratio1: 30-1: 10) to give 1.19 g of compound 4 as a pale yellow liquid in 90percent yield.

The synthetic route of 3344-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guilin University of Technology; Kong, Xiangfei; Dai, Shengping; Yang, Willow; Deng, Sea; Wang, Guixia; (8 pag.)CN106117224; (2016); A;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, 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 955959-84-9, HPLC of Formula: C18H11BrO

Intermediate M-1 in a round bottom flask 10.0g (30.9mmol) and M-32 15.5g (30.9mmol),Sodi um-t- butoxide placed 4.46g (46.35mmol) was dissolved was added to 155ml of toluene. Here Pd2 (dba) 3 0.28g (0.31mmol) and tri-tert-butylphosphine was placed to 0.18g (0.93mmol) in turn and the mixture was stirred under reflux for 12 hours under a nitrogen atmosphere. After the reaction extracted with distilled water and toluene and the organic layer was dried with magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The product n- hexane / dichloromethane (8: 2 by volume) to yield the silica gel column chromatography to give compound 9 as 20.71g (90percent yield).

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

Reference:
Patent; SAMSUNG SDI CO., LTD.; JANG, YU NA; HONG, JIN SEOK; KIM, YOUNG KWON; YU, EUN SUN; KIM, CHANG WOO; KIM, HUN; MIN, SOO HYUN; CHO, PYEONG SEOK; (38 pag.)KR2016/12846; (2016); A;,
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Application of 558-13-4,Some common heterocyclic compound, 558-13-4, name is Carbontetrabromide, molecular formula is CBr4, 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 an ice cold solution of the hexanol (ca. 19.8 mmol) and carbon tetrabromide (21.98 mmol) in methylene chloride (50 ml) was added triphenylphosphine (22.30 mmol) in methylene chloride (50 ml) and the resulting solution was stirred for 2.5 hours. The volatiles were evaporated and the residue was taken up in either (100 ml), cooled in ice, and filtered. The filtrate was evaporated and distilled to afford 6-phenylhexyl bromide as an oil.

The synthetic route of 558-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; US5135938; (1992); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 43204-63-3,Some common heterocyclic compound, 43204-63-3, name is Bis(2-Bromoethyl)amine hydrobromide, molecular formula is C4H10Br3N, 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.

EXAMPLE 35 Preparation of Bis(2-bromoethyl)phosphoramidic dichloride (29) TEA (7.12 g, 70 mmol) was added dropwise to a stirred solution of bis(2-bromoethyl)amine hydrobromide (10.00 g, 32 mmol) and phosphorus oxychloride (4.91 g, 32 mmol) in CH2 Cl2 (50 ml) at 0 C. under N2. The mixture was allowed to stir overnight and then poured over ice. The layers were separated, and the aqueous layer was extracted with CH2 Cl2 (3*50 ml). The organic layers were combined and dried (MgSO4). The filtrate was concentrated under reduced pressure and the residue purified by chromatography (1:4 EtOAc: hexanes) to give 29 as an oil (3.86 g, 35%); 1 H NMR (CDCl3) 3.70 (t, 4H, 6.73 Hz), 3.55 (t, 4H, 6.75 Hz)ppm.

The synthetic route of 43204-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; University of Rochester; US5233031; (1993); A;,
Bromide – Wikipedia,
bromide – Wiktionary

72678-19-4, name is 2,6-Dibromo-4-(trifluoromethyl)aniline, 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. Quality Control of 2,6-Dibromo-4-(trifluoromethyl)aniline

General procedure: A suspension of potassium hydride (3 equiv) in THF (0.6 M) was cooled in an ice-water bath. A solution of sulfonamide, sulfonamide or aniline (1.0 equiv) in THF (0.20 M) was added dropwise, and the suspension was stirred for 15 min. 1,1′-Carbonyldiimidazole (1.0 equiv) was dissolved in 1:1 THF/dioxane (0.20 M) and added dropwise to the reaction mixture, resulting in the formation of a white precipitate. The ice-water bath was removed, and the reaction mixture was allowed to warm to ambient temperature and was stirred for 2 h. A solution of diamine S-1 (1.0 equiv) in THF (1.0 M) was added dropwise, and the suspension was stirred at room temperature for 20 h. The reaction was quenched with a solution of acetic acid (3 equiv) in THF (1.0 M). The crude product was concentrated in vacuo and purified by silica gel chromatography.

The synthetic route of 72678-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kimmel, Kyle L.; Robak, Maryann T.; Thomas, Stephen; Lee, Melissa; Ellman, Jonathan A.; Tetrahedron; vol. 68; 12; (2012); p. 2704 – 2712;,
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Some common heterocyclic compound, 2789-89-1, name is 1,2-Bis(4-bromophenyl)ethyne, molecular formula is C14H8Br2, 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. Application In Synthesis of 1,2-Bis(4-bromophenyl)ethyne

General procedure: Diphenylacetylene (36 mg, 0.20 mmol), NFSI (95 mg, 0.30 mmol,1.5 equiv), bathocuproine (8.7 mg, 24 mumol, 12 mol%), CuBr (2.9 mg, 20 mumol, 10mol%) and CsF (30 mg, 0.20 mmol, 1.0 equiv) were added to a Schlenk tubecontaining a magnetic stirring bar in open air. The tube was evacuated and refilledwith N2 gas following the usual Schlenk technique. Anhydrous 1,2-dichloroethane(2.0 mL, 0.10 M) was added into the tube and the reaction tube was capped with a J.Young O-ring tap. The reaction mixture was stirred and heated at 70 C for 12 h.The mixture was then cooled to room temperature. The crude mixture was filteredthrough a pad of silica gel topped with Na2SO4 in a short column and concentrated invacuo. 2-Fluorobiphenyl (17.2 mg, 0.10 mmol) was added into the crude as aninternal standard and the 19F NMR yield was determined. Purification by flashchromatography on silica gel (hexane/EtOAc = 7:1) followed by concentration invacuo provided 2a in 62% (53.3 mg, 0.124 mmol) yield as white crystals.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2789-89-1, its application will become more common.

Reference:
Article; Yip, Shu Jan; Yoshidomi, Tetsushi; Murakami, Kei; Itami, Kenichiro; Chemistry Letters; vol. 47; 3; (2018); p. 329 – 331;,
Bromide – Wikipedia,
bromide – Wiktionary

955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, 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. Formula: C18H11BrO

475 mg (1.00 mmol) of Intermediate (B), 388 mg (1.20 mmol) of 4-(4-bromophenyl)dibenzo[b,d]furan, 91.6 mg(0.100 mmol) of Pd2(dba)3, 100 mL (50percent in toluene, 0.200 mmol) of tri-tert-butylphosphine (ttbp), and 192 mg (2.00mmol) of sodium tert-butoxide were added to 10 mL of xylene, and then, the mixture was heated at a temperature of145¡ãC while stirring. When the reaction stopped, the reaction product was cooled to room temperature and then subjectedto silica gel to perform filtering under a reduced pressure, and the filtration solution was concentrated under a reducedpressure. The product was subjected to silica gel column chromatography (ethylacetate: n-hexane = 1: 4 volume tovolume). The product was refined by recrystallization using toluene/methanol to obtain 465 mg (yield of 65percent) of Compound1 as a target compound. LC-Mass (calculated: 715.26 g/mol, found: M+1 = 716 g/mol)

The synthetic route of 955959-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung Electronics Co., Ltd; Samsung SDI Co., Ltd.; Jung, Yongsik; Son, Jhunmo; Lee, Seungjae; Kim, Youngkwon; Kim, Hyungsun; Chung, Yeonsook; EP2878599; (2015); A1;,
Bromide – Wikipedia,
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