Tag: M.W=200-300

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. 69321-60-4, name is 2,6-Dibromotoluene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,6-Dibromotoluene

3-Bromo-2-methylbenzonitrile. This compound was prepared in a manner similar to that described for 3-bromo-5-fluorobenzonitrile from commercially available 2,6-dibromotoluene (1.80 g, 7.20 mmol), DMF (11 mL), pyridine (1.1 mL), and copper (I) cyanide (0.52 g, 5.76 mmol). The crude product was purified by flash column chromatography (100 mL silica, hexane) to afford 50 mg (35%) of 3-bromo-2-methylbenzonitrile.

According to the analysis of related databases, 69321-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 771583-12-1, A common heterocyclic compound, 771583-12-1, name is 2-(Aminomethyl)-4-bromoaniline, molecular formula is C7H9BrN2, 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 2: 6-bromo-3.4-dihvdroquinazolin-2(1 H)-one; To a solution of triphosgene (0.445 g, 1.5 mmol) in tetrahydrofuran (20 mL) was added triethylamine (0.454 g, 4.5 mmol) dropwise at 0 0C under nitrogen. After stirring for 30 min, a solution of 2-(aminomethyl)-4-bromoaniline (0.201 g, 1 mmol) in tetrahydrofuran (10 mL) was added dropwise. The mixture was allowed to stir for 16 h at room temperature. The mixture was diluted with water (15 mL) and the pH of the resultant mixture was adjusted to 8 – 9 by the addition of 1 M aqueous sodium hydroxide. The mixture was extracted three times with ethyl acetate (30 mL). The combined organic layer was dried over sodium sulfate and concentrated. The residue was purified by re- crystallization from a mixture o dichloromethane and diethyl ether to give the title compound (0.13 g, 57.5%) as a yellow solid. 1 H NMR (400MHz, DMSO-Cf6) delta ppm 9.12 (s, 1 H), 7.29 (S, 1 H), 7.27(d, J = 8.4 Hz, 1 H), 6.87 (s, 1 H), 6.70 (d, J = 8.4 Hz, 1 H), 4.28 (s, 2H).

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:
Patent; PFIZER INC.; ARHANCET, Graciela Barbieri; CASIMIRO-GARCIA, Agustin; CHEN, Xiangyang; HEPWORTH, David; MEYERS, Marvin Jay; PIOTROWSKI, David Walter; RAHEJA, Raj Kumar; WO2010/116282; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 22385-77-9,Some common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, molecular formula is C14H21Br, 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.

The bromide (2.0 g, 7.4 mmol), tri-nbutyi-1-ethoxyvinyl tin (3.2 g, 8.9 mmol), and PdCl2(Ph3P)2 ( 522 mg, 0.74 mmol) were dissolved in toluene 3.7 mL and the solution stirred at 95 0C for 3 hours. The volatiles were removed in vac. and the residue dissolved in 1,4-dioxane (33 mL). Aqueous HCl (2 N, 1 1 mL) was added and the solution stirred rapidly at RT for 1 hour. The mixture was diluted with water (350 mL), followed by aqueous/EtOAc work-up and silica gel chromatography (diethyl ether: hexanes (1 :9)) to give the titled compound.

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-3,5-di-tert-butylbenzene, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2007/64553; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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. Safety of 1-Bromo-3,5-di-tert-butylbenzene

Production Example 2 of Optically Active AminoalcoholA 200 mL round-bottom four-neck flask equipped with a Dimroth condenser with a nitrogen introducing tube attached thereto, a thermometer, a magnetic rotator and a dropping funnel was heated under reduced pressure, nitrogen was then introduced into the flask, pressure in the flask was returned to normal pressure, and the flask was cooled to room temperature. After 1.27 g of magnesium and a minor amount of iodine were added to the flask, a small amount of a solution obtained by mixing 15.00 g of 3,5-di-tert-butylbromobenzene and 75.0 mL of dehydrated tetrahydrofuran was added dropwise. The flask was heated, and it was confirmed that the Grignard reaction was initiated. Thereafter, the remaining solution was added dropwise to the flask over 30 minutes. The resulting mixture was refluxed for 1.5 hours. After the resulting reaction mixture was cooled to -10° C., 1.11 g of L-valine methyl ester hydrochloride was added. After the temperature of the resulting mixture was raised to room temperature, the mixture was further refluxed for 4 hours. The resulting reaction mixture was cooled to 0 to 5° C. To the reaction solution were added dropwise 45.0 mL of an aqueous saturated ammonium chloride solution, and further 15.0 mL of water. The resulting mixture was stirred at 20° C. for 30 minutes. The resulting mixture was extracted with 45.0 mL of diethyl ether three times. The resulting organic layers were mixed, and dried with anhydrous sodium sulfate. After sodium sulfate was removed by filtration, the resulting filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/9840/60) to obtain 1.02 g of a colorless crystal of (S)-2-amino-1,1-di(3,5-di-tert-butylphenyl)-3-methyl-1-butanol.1H-NMR (300 MHz, CDCl3, TMS standard)delta (ppm): 7.54 (2H, d), 7.43 (2H, d), 7.28 to 7.24 (2H, m), 4.23 (1H, brs), 3.80 (1H, d), 1.77 (1H, m), 1.35 (18H, s), 1.33 (18H, s), 1.32 (2H, s), 0.96 (3H, d), 0.87 (3H, d)13C-NMR (75 MHz, CDCl3, TMS standard)delta (ppm): 150.86, 150.43, 147.46, 144.67, 121.01, 120.80, 120.76, 120.38, 81.24, 62.12, 35.67, 35.61, 32.33, 32.27, 28.60, 23.88, 17.09

The synthetic route of 1-Bromo-3,5-di-tert-butylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Masumoto, Katsuhisa; Yoshikawa, Kouji; US2011/166372; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 2635-13-4, 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. 2635-13-4 name is 5-Bromobenzo[d][1,3]dioxole, 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.

A heavy-walled tube was charged with 5.01 grams (3 ml, 24.896 mmol) ofcommercially available 5-bromo-1,3-benzodioxole followed by dry DMF (5ml) followed by copper iodide (0.474 grams, 2.490 mmol, 0.10 equivalents), PdCl2(PPh3)2 (0.349 grams, 0.4979 mmol, 0.02 equivalents), and triethylamine (35 ml) and then subjected tooxygen removal using a freeze-pump-thaw method. Finally TMS-acetylene (3.68 grams, 5.3 ml,37.34 mmol) was then added and the tube was quickly sealed and heated in an oil bath at 90 Cfor 24 hours. At this time the reaction was cooled and worked up by concentration in vacuo andsubmitted to flash chromatography using straight hexanes to afford compound weighing 3.4 g.Yield is 62 %.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromobenzo[d][1,3]dioxole, and friends who are interested can also refer to it.

Reference:
Article; Abrams, Jason N.; Zhao, Qi; Ghiviriga, Ion; Minaruzzaman; Tetrahedron; vol. 68; 2; (2012); p. 423 – 428;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 7499-66-3, The chemical industry reduces the impact on the environment during synthesis 7499-66-3, name is 6-Bromonaphthalen-2-amine, I believe this compound will play a more active role in future production and life.

According to a known method described in a reference [L. C. Anderson et al., Journal of the American Chemical Society (J. Am. Chem. Soc.), vol. 65, p.241, 1943], a solution of 2-amino-6-bromonaphthalene (223 mg) obtained from commercially available 2-bromo-6-hydroxynaphthalene (TCI) in anhydrous THF (10 ml) was added with 30percent potassium hydride (191 mg, Ald) under ice cooling and stirred for 1 hour. The reaction mixture was cooled to -78° C. under argon atmosphere, added dropwise with-1.7 M solution of t-butyllithium in pentane (1.88 ml) over 10 minutes and stirred for 30 minutes. The reaction mixture was added dropwise with (iPrO)3B (0.92 ml) over 10 minutes, stirred for 30 minutes, then warmed to room temperature and further stirred for 3 hours. The reaction mixture was added with water (3 ml) and 0.5 M aqueous sulfuric acid (4 ml) and extracted with diethyl ether (100 ml.x.3). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain crude 6-amino-2-naphthaleneboronic acid (402 mg). According to the procedure described in the synthesis method of Compound of Example 001 (Preparation Method 4, Step d-1) with the modifications that the reaction was carried out for 13 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=4:1), a solution of the above compound in ethanol (0.5 ml), Intermediate 3 (119 mg), 2 M aqueous sodium carbonate (1.5 ml) and (Ph3P)4Pd (61 mg) were reacted and treated to obtain the title compound (Compound No. 011, 129 mg).

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, 6-Bromonaphthalen-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shoda, Motoshi; Kuriyama, Hiroshi; US2004/44258; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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;,
Bromide – Wikipedia,
bromide – Wiktionary

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;,
Bromide – Wikipedia,
bromide – Wiktionary

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;,
Bromide – Wikipedia,
bromide – Wiktionary

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,
bromide – Wiktionary