Month: July 2021

Application of 6274-57-3,Some common heterocyclic compound, 6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, molecular formula is C9H12BrN, 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.

General procedure: At room temperature, organic carbonyl acid 3 (R-COOH, 0.5 mmol) was added into a reaction tube equipped with a small magnet. Then a solution of tertiary amine 1 (R1CH2-NR2R3, 0.5 mmol ) in DCM (2.5 mL) was added dropwise in 2 min. After the mixture was stirred at room temperature for a few minutes, 1 equivalents of dimethyl acetylenedicarboxylate (DMAD, 2) was added. The reaction was stirred overnight at room temperature, and then monitored by TLC with silica gel coated plates. After being stirred for 14 h, the solvent was removed and the residue was purified by a flash column chromatography with silica gel with ethyl acetate/hexane (1:25-30) as eluent to give the desired products 4, 5, and 7. Most of compounds are known and confirmed by NMR, ESI-MS, IR.

The synthetic route of 6274-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shen, Hao; Lu, Xing; Jiang, Ke-Zhi; Yang, Ke-Fang; Lu, Yixin; Zheng, Zhan-Jiang; Lai, Guo-Qiao; Xu, Li-Wen; Tetrahedron; vol. 68; 43; (2012); p. 8916 – 8923;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 61613-22-7, 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. 61613-22-7, name is 2-Bromo-N-phenylaniline, This compound has unique chemical properties. The synthetic route is as follows.

In a 200 mL three-neck flask equipped with a reflux tube, BrDPA (4.96 g, 20 mmol), di-tert-butyl dicarbonate (7.7 ml, 35 mmol), N, N-dimethyl-4-aminopyridine (0.37 g) , 3 mmol) and 150 ml of dehydrated tetrahydrofuran. The mixture was heated to reflux for about 20 hours. When the progress of the reaction was confirmed by TLC, consumption of the raw materials and spots that seemed to be the target substance were confirmed. The reaction was terminated, and the temperature was returned to room temperature. After returning to room temperature, concentration was performed. Thereafter, purification was performed by column chromatography (developing solvent ratio: n-hexane: dichloromethane = 1: 1) to obtain 5.89 g (yield = 85%) of the desired product. Identification was performed by 1H-NMR.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-N-phenylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Flask Co., Ltd.; Sasabe, Hisahiro; Kido, Junji; Arai, Hiroki; Nakao, Kohei; (21 pag.)JP2020/26399; (2020); A;,
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. 34950-82-8, name is 7-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine, A new synthetic method of this compound is introduced below., Computed Properties of C7H7BrN2O

To a solution of 7-bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine (1.50 g, 6.98 mmol) in THF (10.0 mL) was added dropwise NaH (307 mg, 7.67 mmol, 60% purity) at 0C. After addition, the mixture was stirred at 0C for 30 mins, and then CH3I (1.09 g, 7.67 mmol, 478 uL) was added dropwise at 0C. The resulting mixture was stirred at 0C for 30 mins. The reaction mixture was extracted with EtOAc (10.0 mL x 3) and H2O (10.0 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give intermediate (G2.D) (1.78 g, crude) as a yellow solid which was without purfication

The synthetic route of 34950-82-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GenKyoTex Suisse SA; MACHIN, Peter; CHAMBERS, Mark; HODGES, Alastair; SHARPE, Andrew; WISHART, Grant; PERRY, Benjamin; CELANIRE, Sylvain; HEITZ, Freddy; (94 pag.)EP3628669; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 4333-56-6,Some common heterocyclic compound, 4333-56-6, name is Bromocyclopropane, molecular formula is C3H5Br, 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.

Intermediate 30: (2S)-Lambda/-r(S)-cvclopropyl(phenyl)methvH-3-methyl-1 -f(trimethylsilyl)oxyl- 2-butanamine Cyclopropyl bromide (4.64g, 38.4mmole) was dissolved in dry diethyl ether (50ml) under argon, cooled to -780C and treated with tert-BuLi (45ml_ of a 1.7M solution in pentane, 76.5mmole). After 10 minutes, cooling was removed and the mixture stirred at room temperature for 1 hr. After re-cooling to -4O0C, a solution of Intermediate 28 (8.43g, 32mmole) in dry diethyl ether (40ml) was added and stirring continued at – 4O0C for 1.5 hrs. 5M HCI acid was added (50ml) and the phases separated. The aqueous phase was washed with diethyl ether (discarded) and then basified with KOH pellets to pH >10 in the presence of diethyl ether. The organic phase was washed with water and brine and then evaporated to dryness under vacuum to afford the title compound as a colourless oil (6.42g, 86%); 1 HNMR (400MHz, CDCI3): delta 0.13 – 0.15, (1 H, m), 0.34 – 0.37, (2H, m), 0.60 – 0.70, (1 H, m), 0.83, (3H, d, J = 7Hz), 0.91 , (3H, d, J = 7Hz), 0.98 – 1.00, (1 H, m), 1.71 – 1.77, (1 H, m), 2.44 – 2.48, (1 H, m), 3.00, (1 H, d, J = 8Hz), 3.32 and 3.36, (1 H, dd, J = 5 and 11 Hz), 3.59 and 3.61 , (1 H, dd, J = 5 and 11 Hz), 7.25 – 7.42, (5H, m); m/z(APCI): 234.2 [M+H]+.

The synthetic route of 4333-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/50991; (2006); 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. 4333-56-6, name is Bromocyclopropane, A new synthetic method of this compound is introduced below., Application In Synthesis of Bromocyclopropane

A solution of cyclopropyl bromide (22. 3 mL, 278 mmol) in diethyl ether (20 mL) was slowly added to a cooled suspension (0 C) of crushed lithium (5.8 g, 834 mmol) in ether (380 mL) (exothermic) under a nitrogen atmosphere. The reaction mixture was stirred for 90 minutes while the temperature rose to room temperature. The solution of this lithiate was slowly added to a cooled solution (0 C) ofN-methoxy-N-methyl-3, 3- [1, 2-ethanediylbis (oxy) ] estra- 5 (10), 9 (11), 16-triene-17-carboxamide (59.7 g, 139 mmol) in THF (260 mL). After stirring this mixture for 2 hours at 0 C, a saturated aqueous NILCl solution was added dropwise (exothermic) followed by water. The organic layer was separated and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated to dryness. The crude product was purified by column chromatography (Si02, heptane/ethyl acetate, 4/1) to give 17- (cyclopropylcarbonyl) estra- 5 (10), 9 (11), 16-trien-3-one cyclic 1,2-ethanediyl acetal (33.9 g, 93 mmol, 67% yield).’H NMR (400 MHz, CDC13) : 8 0.82-2. 67 (m, 24H), 3.99 (s, 4H), 5.59 (m, 1H), 6.88 (m, 1H).

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; AKZO NOBEL N.V.; WO2005/92912; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 399-94-0, A common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, 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.

Reference Example-71 THF (25 mL) was added to metal magnesium (2.55 g, 105 mmol), and 2-bromo-1,4-difluoro benzene (19.70 g, 100 mmol) was slowly added thereto, whereby a Grignard reagent was prepared. The previously prepared Grignard reagent was added dropwise to the separately prepared solution of diethyl oxalate (15.34 g, 105 mmol) in THF (10 mL) at -40 C. or lower. After the dropping was completed, the reaction temperature was raised to 0 C., followed stirring for 1 hour. A saturated ammonium chloride aqueous solution and water (200 mL) were added to the reaction solution, and the resultant product was extracted with ethyl acetate (200 mL*2). After the organic layer was dried over magnesium sulfate and filtered, the solvent was distilled off under reduced pressure, and the resultant product was distilled under reduced pressure, whereby ethyl 2-(2,5-difluorophenyl)-2-oxoacetate (14.82 g, yield: 62%) was obtained as a colorless liquid. 1H-NMR (400 MHz, CDCl3): delta1.40 (t, J=7.0 Hz, 3H), 4.44 (q, J=7.0 Hz, 2H), 7.16 (ddd, J=9.3, 9.3 and 4.0 Hz, 1H), 7.34 (dddd, J=9.3, 9.2, 7.3 and 3.3 Hz, 1H), 7.60 (ddd, J=8.2, 5.3 and 3.3 Hz, 1H). 19F-NMR (376 MHz, CDCl3): delta-116.9 (d, J=7.8 Hz, 1F), -116.3 (d, J=7.8 Hz, 1F).

The synthetic route of 399-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; SAGAMI CHEMICAL RESEARCH INSTITUTE; KOBAYASHI, Osamu; NIIKURA, Naoko; INOUE, Tomoko; MIZUTA, Satoshi; TAKATSUNA, Reiko; HIRAI, Kenji; SHIROUZU, Kentaro; OBATA, Miyoo; (183 pag.)US2016/24110; (2016); 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. 49764-63-8, name is 4,5-Dibromobenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H6Br2N2

iert-butyl (1-(5,6-dibromo-1 H-benzo[d]imidazol-2-yl)-2-(4- methoxyphenyl)ethyl)carbamate: In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-((terf-butoxycarbonyl)amino)-3-(4- methoxyphenyl)propanoic acid (500 mg, 1.69 mmol) in AcCN (16.9 mL) was treated at rt with 4-ethylmorpholine (0.43 mL, 3.39 mmol), TBTU (544 mg, 1.69 mmol) and 4,5- dibromobenzene-1 ,2-diamine (450 mg, 1.69 mmol). The reaction mixture was stirred at rt until completion. The reaction mixture was diluted with EA and water. The org. phase was dried over MgS04, filtered, and the solvent was removed under reduced pressure. The residue was dissolved in glacial acetic acid (25 mL) and the reaction mixture was stirred at 60 C for 1 h. The mixture was cooled to rt and the solvent was removed under reduced pressure. The residue was partitioned between EA (25 mL) and sat. aq. NaHC03 (25 mL). The org. layer was washed with sat. aq. NaHC03 (twice 25 mL), dried over MgS04, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (4:6 EA-heptane) gave the title compound as beige solid: TLC: rf (4:6 EA-heptane) = 0.35. LC-MS-conditions 12: tR = 0.88 min; [M+H]+ = 525.61.

According to the analysis of related databases, 49764-63-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CORMINBOEUF, Olivier; CREN, Sylvaine; LEROY, Xavier; POZZI, Davide; WO2015/19325; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 138526-69-9

(a) To 50 ml of N-methylpyrrolidone were added 10 g of 3,4,5-trifluorobromobenzene and 8.5 g of copper cyanide, and the resulting mixture was stirred at 150C for 4 hours. Thereafter, aqueous ammonia was added to the reaction mixture which had been allowed to cool to near room temperature, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 5.0 g of 3,4,5-trifluorobenzonitrile was obtained.

The synthetic route of 138526-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2151432; (2010); 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. 50548-45-3, name is 1-Bromodibenzo[b,d]furan, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

Compound B-3 (40 g, 161.9 mmol) was dissolved in acetic acid (200 mL). To this was added iodine (4.16 g, 81.0 mmol), iodic acid (6.3 g, 36.0 mmol), and sulfuric acid (10 mL) and the mixture was stirred at 65 C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and water was added thereto. The resulting solid was filtered, washed with water and then recrystallized with toluene and ethyl acetate to obtain 50.1 g (yield: 83%;

The synthetic route of 50548-45-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; Jeong Min-u; Lee Dong-hun; Park Tae-yun; Cho Seong-mi; Lee Jeong-ha; Lee Ju-yeong; (32 pag.)KR2018/76357; (2018); A;,
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. 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-N1-methylbenzene-1,2-diamine

B) Methyl (1RS,2SR)-2-(6-bromo-1-methyl-1H-benzimidazol-2-yl)cyclopropanecarboxylate [0305] O-(7-Azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (554 mg) was added to a solution of 4-bromo-N2-methylbenzene-1,2-diamine (279 mg), diisopropylethylamine (0.727 mL) and (1RS,2SR)-2-(methoxycarbonyl)cyclopropanecarboxylic acid (200 mg) in DMF (5 mL) at room temperature. The mixture was stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The obtained residue was dissolved in acetic acid (5 mL), and the mixture was stirred at 80C for 1 hr. After concentration of the reaction mixture, saturated sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The obtained residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (80 mg) as a pale brown solid. MS (ESI+):[M+H]+ 309.1. 1H NMR (400 MHz, DMSO-d6) delta 1.55 (1H, dt, J = 8.4, 4.3 Hz), 1.72-1.80 (1H, m), 2.26-2.36 (1H, m), 2.74 (1H, q, J = 8.4 Hz), 3.41 (3H, s), 3.72 (3H, s), 7.28 (1H, d, J = 8.5 Hz), 7.49 (1H, d, J = 8.5 Hz), 7.76 (1H, s).

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; Takeda Pharmaceutical Company Limited; KASAI, Shizuo; IGAWA, Hideyuki; TAKAHASHI, Masashi; KINA, Asato; EP2848621; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary