Category: bromides-buliding-blocks

Synthetic Route of 314084-61-2,Some common heterocyclic compound, 314084-61-2, name is 2-Bromo-1,3-diethyl-5-methylbenzene, molecular formula is C11H15Br, 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.

21.5 g of sodium ethanolat and 150 g of 1-methyl-2-pyrrolidone are mechanically stirred under a nitrogen atmosphere and at normal pressure. 7.3 g of malonic acid dinitrile are added thereto in portions. 58 g of diluent are distilled off at from 100 to 120C under reduced pressure (from 20 to 30 mbar). Under a nitrogen atmosphere and at normal pressure, 22.7 g of 2-bromo-1, 3-diethyl-5-methylbenzene are added at 110C. The reaction mixture is heated to 125C. At that temperature, a mixture of 0.13 g of TRIPHENYLPHOSPHINE, 0.1 g of a commercially available palladium (lI) chloride solution in concentrated hydrochloric acid (20% Pd content corresponding to 0.035 g of PALLADIUM (II) CHLORIDE in 0.071 g of concentrated hydrochloric acid) and 9.6 g of 1-methyl-2-pyrrolidone is added. The reaction mixture is heated at from 120 to 130C for 1 hour. A mixture of 0.13 g of triphenylphosphine, 0.1 g of a commercially available palladium (II) chloride solution in concentrated hydrochloric acid (20% Pd content corresponding to 0.035 g of palladium (li) chloride in 0.071 g of concentrated hydrochloric acid) and 9.6 g of 1-methyl-2-pyrrolidone is again added. The reaction mixture is stirred for 2 hours at from 120 to 130C. A gas chromatogram of a sample (1 ml of reaction mixture partitioned between 2 ml of 1 N hydrochloric acid and 2 ml of tert-butyl methyl ether) shows that the product (2- (2, 6-diethyl- 4-methylphenyl) malonic acid dinitrile) has not formed.

The synthetic route of 314084-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2004/50607; (2004); A1;,
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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. 656-64-4, name is 3-Bromo-4-fluoroaniline, A new synthetic method of this compound is introduced below., Safety of 3-Bromo-4-fluoroaniline

A solution of sodium nitrite (4.2 g , 60 mmol) was added drop-wise to a mixture of 3-bromo-4-fluoroaniline (11.2 g, 58.9 mmol) and concentrated HCl (30 mL, 0.36 M) at 0 0C over 30 min. The resulting clear solution was stirred for 45 min, and a solution of SnCl2*2H2O (27 g, 120 mmol) in concentrated HCl (30 mL) was added drop-wise at 0 0C over 1.5 h. The mixture was stirred for 18 h at room temperature. The resulting precipitate was collected by filtration and crystallized from ethanol to provide the title compound (6.2 g, 42 %) as a yellow powder: 1H NMR (300 MHz, DMSO-J6) delta 10.24 (s, 3H), 8.42 (s, IH), 7.36-7.30 (m, 2H), 7.03-6.98 (m, IH).

The synthetic route of 656-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; WO2009/89482; (2009); A1;,
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142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, 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: C7H3BrF4

Example 26 Synthesis of TRV 1 158[00166] TRV 1158 – phenyl(4-(3-(pyrrolidin- l -yl)-4-(trifluoromethy])phenyl)piperazin- l – yl)methanone[00167] Scheme for TRV 1 158DIPEA / N P[00168] A mixture of 4-bromo-2-fluorobenzotrifluoride ( l .5 l l g, 6.2 mmol), pyrrolidine (0.62 mL, 7.46 mmol), DIPEA ( 1.6 mL, 9.33 mmol) and NMP (8 mL) were sealed in a tube and heated to 120 C overnight. The solution was cooled to room temperature and diluted with water and EtOAc. The layers were separated and the aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed successively with H2O, IN HCl(aq), saturated NaHC03(aq), H2O, and brine before drying with Na2SC>4. The mixture was filtered and concentrated to give a crude oil, which was purified via flash chromatography (5 % EtOAc / hexane) to give 0.9667 g (53 % yield) of desired product. This bromo-intermediate (0.5312 g, 1.8 mmol), benzoylpiperazine hydrochloride (0.4987 g, 2.2 mmol) and NaO/Bu (0.5189 g, 5.4 mmol) were charged to a flask which was subsequently purged and evacuated with argon (3 cycles). Toluene (5.4 mL) and NMP (3.2 mL) were then added and the solution was degassed for 30 minutes before added Pd2(dba)3 (0.033 g, 0.036 mmol) and BINAP (0.045 g, 0.072 mmol) all at once. The flask was then heated to 100 C overnight under argon. The mixture was cooled to room temperature and diluted with EtOAC before filtering through Celite. The organic layer was then washed successively with H20, IN HCl(aq), saturated NaHC03(aq), H2O, and brine before drying with Na2S04. The mixture was filtered and concentrated to give 0.5081 g of crude oil. The oil was purified via flash chromatography (45 % EtOAc / hexane) to give another crude oil that was slightly impure. This oil was crystallized from EtOAc (solvent) and hexane (anti-solvent) to give 0.101 g of white crystals of TRV 1158, phenyl(4-(3-(pyrrolidin-l -yl)-4- (trifluoromethyl)phenyl)piperazin- l-yl)methanone. NMR (500 MHz, DMSO) delta = 7.47-7.41 (m, 5H), 7.35 (d, J = 8.5 Hz, 1 H), 6.49 (dd, J = 8.5, 1.5 Hz, 1 H), 6.46 (m, 1 H), 3.72 (br s, 2H), 3.45 (br s, 2H), 3.30 (br s, 4H), 3.23-3.20 (m, 4H), 1.88- 1.83 (m, 4H).

The synthetic route of 142808-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TREVENTIS CORPORATION; REED, Mark, A.; YADAV, Arun; BANFIELD, Scott, C.; BARDEN, Christopher, J.; WO2012/119035; (2012); A1;,
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Synthetic Route of 2550-36-9, These common heterocyclic compound, 2550-36-9, name is (Bromomethyl)cyclohexane, 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 1 : To a solution of 3-bromo-6-methylimidazo[1,5-a]pyrazin-8(7H)-one (1 g, 4.39 mmol, 1 eq) and Cs2CO3 (2.86 g, 8.78 mmol, 2 eq) in DMF (20 mL) was added (bromomethyl)cyclohexane (1.55 g, 8.78 mmol, 1.22 mL, 2 eq). The mixture was stirred at 60C for 18 hour. The reaction mixture was filtered and the filtrate was concentrated. The crude mixture was purified by flash chromatography with petroleum ethenethyl acetate = 5:1 ~ 3: 1. 3-bromo-7-(cyclohexylmethyl)-6-methylimidazo[1,5-a]pyrazin-8(7H)-one (1 g, 3.02 mmol, 69% yield) was obtained. 1H NMR (CDCl3 , 400 MHz): delta 7.86 (s, 1 H), 6.80 (s, 1 H), 3.79 (6, J = 1.2 Hz, 2H), 2.29 (s, 3H), 1.75 -1.66 (m, 6H), 1.22 – 1.04 (m, 5H). LC-MS: tR = 0.791 min (method 15), m/z = 325.9 [M + H]+.

The synthetic route of 2550-36-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2606-51-1, name is 5-(Bromomethyl)benzo[d][1,3]dioxole, 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 2606-51-1, Application In Synthesis of 5-(Bromomethyl)benzo[d][1,3]dioxole

General procedure: A mixture of benzyl bromide (171 mg, 1 mmol), diphenyl disulfide (131 mg, 0.6 mmol), PPh3 (184 mg, 0.7 mmol), and [pmIm]Br21 (94 mg, 0.4 mmol) was stirred at 75 C for 1.5 h (TLC). The reaction mixture was extracted with Et2O, and the organic layer was washed with brine (2 × 5 mL) and dried (Na2SO4). Evaporation of solvent left the crude product which was purified by column chromatography over silica gel (hexane) to afford the pure product, benzyl phenyl sulfide (168 mg, 84%) as a colorless liquid. The remaining ionic liquid was washed with ether, dried under vacuum, and reused five times without appreciable loss of catalytic activity.

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; Banerjee, Subhash; Adak, Laksmikanta; Ranu, Brindaban C.; Tetrahedron Letters; vol. 53; 17; (2012); p. 2149 – 2152;,
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Related Products of 460-00-4, 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. 460-00-4, name is 1-Bromo-4-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of a fluorinated aryl halide (2.0 mmol), a carbazole (0.5 mmol), and a base (2.0 mmol) in solvent (2 mL) was allowed to react under air atmosphere. The reaction mixture was heated to the specified temperature for 24 h. After reaction completion, the mixture was added to brine (15 mL) and extracted with CH2Cl2 (3 × 15 mL). The combined extract was concentrated under reduced pressure and the product was isolated by short chromatography on a silica gel (200-300 mesh) column.

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

Reference:
Article; Wang, Lei; Ji, Enhui; Liu, Ning; Dai, Bin; Synthesis; vol. 48; 5; (2016); p. 737 – 750;,
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Electric Literature of 399-94-0,Some common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, 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.

2-Bromo-l,4-difluorobenzene(53.6 g, 277.74 mmol) in THF cooled to -50C was added to isopropyl magnesium chloride (2M in THF)( 133mL, 266 mmol). The reaction mixture thus obtained was warmed to 0C and stirred for lh. The reaction mixture was cooled again to -50C. 4-chloro-N-methoxy-N-methylbutanamide (40 g, 241.52 mmol) in THF (200mL) was added dropwise to this reaction mixture with stirring and the stirring was continued at 0C for lh. The reaction mixture was quenched with saturated aqueous NH4C1 solution, extracted with ethylacetate. The organic layer collected was washed with water (500 mL) and then with brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a crude liquid residue. The residue thus obtained was purified by column chromatography (using 60-120 silica gel and 5% EtOAc in Hexane as eluent) to afford 35 g of the title compound as a colourless liquid. 1H NMR (300MHz, CDC13) delta ppm 7.6-7.53(lH, m), 7.26-7.09(2H, m), 3.7(2H, t) 3.22- 3.14(2H, m), 2.28-2.16(2H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2,5-difluorobenzene, its application will become more common.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; SASMAL, Pradip Kumar; AHMED, Shahadat; TEHIM, Ashok; PRADKAR, Vidyadhar; DATTATREYA, Prasanna M.; MAVINAHALLI, Nanjegowda Jagadeesh; WO2013/88256; (2013); A1;,
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Synthetic Route of 55289-36-6, 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 55289-36-6 as follows.

A mixture of 3-bromo-2-methylaniline (10 mL, 60.52 mmol), chloral hydrate (14.86 g, 89.86 mmol) and anhydrous Na2S04 (94.56 g, 665.74 mmol) in hydrochloric acid (6.4 mL, 21 1.24 mmol) and H2O (700 mL) was stirred vigorously at room temperature overnight. To the resulting mixture, hydroxylamine hydrochloride (5.86 g, 84.26 mmol) was added and the mixture was heated to reflux overnight. The reaction mixture was ice cooled, and the resulting precipitate was collected by vacuum filtration and washed copiously with H2O and dried under suction. The precipitate was re-dissolved in EtOAc (-500 mL) and washed with H2O (300 mL) and brine (300 mL) then dried over MgS04. The resulting filtrate was removed in vacuo to give 6-bromo-7-methyl-indoline-2,3-dione as a dark brown solid in quantitative yield, which was used directly in the next step without further purification. LC-MS 238.5/240.5 [M+H]+; RT 1.84 min

According to the analysis of related databases, 55289-36-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; REDX PHARMA PLC; STOKES, Neil; (163 pag.)WO2017/46603; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 65896-11-9, name is 2-Bromo-6-fluoroaniline, 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 65896-11-9, Quality Control of 2-Bromo-6-fluoroaniline

[0676] 2-Propylzinc bromide (0.50 M in THF, 16 mL, 7.9 mmol, Sigma-Aldrich Corporation, St. Louis, MO, USA) was added to a stirred mixture of 2-bromo-6-fluoroaniline (1.00 g, 5.26 mmol, Acros, Geel, Belgium), palladium (II) acetate (0.059 g, 0.263 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethylamino-1,1′-biphenyl (0.230 g, 0.526 mmol, Strem Chemicals, Newburyport, MA) in THF (10 mL), and the resulting mixture was stirred under Ar(g) in a sealed vial at rt for 3 h. The reaction mixture was then diluted with satd. aq. ammonium chloride and extracted with EtOAc. The organic extract was then washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, eluent: 0-25% EtOAc in heptane) gave 2-fluoro-6-isopropylaniline as a yellow oil (Intermediate I-26, 618 mg, 4.03 mmol, 77 % yield).1H NMR (400 MHz, CDCl3) d ppm 6.92 (1H, d, J=7.88 Hz) 6.86 (1H, ddd, J=10.73, 8.14, 1.24 Hz) 6.69 (1H, td, J=7.88, 5.60 Hz) 3.70 (2 H, br s) 2.92 (1H, spt, J=6.84 Hz) 1.26 (6 H, d, J=6.84 Hz). m/z (ESI, +ve ion): 154.1 (M+H)+.

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; AMGEN INC.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; MINATTI, Ana Elena; XUE, Qiufen; WURZ, Ryan Paul; TEGLEY, Christopher M.; PICKRELL, Alexander J.; NGUYEN, Thomas T.; MA, Vu Van; LOPEZ, Patricia; LIU, Longbin; KOPECKY, David John; FROHN, Michael J.; CHEN, Ning; CHEN, Jian Jeffrey; SIEGMUND, Aaron C.; AMEGADZIE, Albert; TAMAYO, Nuria A.; BOOKER, Shon; GOODMAN, Clifford; WALTON, Mary; NISHIMURA, Nobuko; SHIN, Youngsook; LOW, Jonathan D.; CEE, Victor J.; REED, Anthony B.; WANG, Hui-Ling; LANMAN, Brian Alan; (738 pag.)WO2019/213516; (2019); A1;,
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Synthetic Route of 67567-26-4, A common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, molecular formula is C6H4BrF2N, 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.

Example 3((1R)-1-{3,5-DIFLUORO-4-[(METHYLSULFONYL)AMINO]PHENYL}ETHYL)-6-(TRIFLUORO-METHYL)QUINOLINE-2-CARBOXAMIDE 3A) N-(4-BROMO-2,6-DIFLUOROPHENYL)METHANESULFONAMIDE To a solution of 4-bromo-2,6-difluoroaniline (3.0 g, 14.4 mmol) in pyridine (20 ml) was added methanesulfonyl chloride (2.23 ml, 28.8 mmol) at room temperature. Then the mixture was stirred at 50 C. for 6 hours. After cooing to room temperature, the mixture was concentrated in vacuo. The resulting residue was dissolved in THF (40 ml). To this solution was added 2M sodium hydroxide aqueous solution (40 ml) and the reaction was stirred at room temperature for 4 hours. The mixture was acidified with 2M HCl aqueous solution and extracted with EtOAc. The organic layer was washed with 2M HCl aqueous solution and brine, dried over sodium sulfate and concentrated in vacuo, to give the title compound (4.05 g, 98%) as an orange solid.1H NMR (270 MHz, CDCl3) delta 3.22 (3H, s), 6.08 (1H, br s), 7.17-7.24 (2H, m).MS (ESI) m/z 286 (M+H)+, 284 (M-H)-.

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; RENOVIS, INC.; US2012/88746; (2012); A1;,
Bromide – Wikipedia,
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