Category: bromides-buliding-blocks

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. 766-81-4, name is 3-Bromophenylacetylene, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H5Br

Step b); Preparation of 1-(3-bromo-phenyl)-2-[5-propionyl-1-(2,2,2-trifluoro-ethyl)-1H-pyrrole-3-yl]-ethane-1,2-dione; A mixture of 1-[4-Iodo-1-(2,2,2-trifluoro-ethyl)-1H-pyrrole-2-yl)-propan-1-one (4.8 g, 0.145 mol), 1-bromo-3-ethynyl-benzene (2.62 g, 0.145 mol) CuI (137 mg, 0.725 mmol) and Pd(PPh3)4 (670 mg, 0.58 mmol) in a mixture of triethylamine (50 ml) and acetonitrile (20 ml) is heated to reflux for 2 hours before cooled down to room temperature. The volatile solvent is removed under reduced pressure, and the residue is partitioned between ethyl acetate (50 ml) and water (200 ml). The organic phase is dried with MgSO4 and is purified by flash chromatography with EtOAc/hexane (10/90-20/80) as eluent to afford the alkyne product as a yellow solid 4.6 g (82%). This solid stirred with KMnO4 (4.73 g, 2.5 mol), NaHCO3 (604 mg, 7.2 mmol) and MgSO4(2.16 g, 18 mmol) in a mixture of acetone (200 ml) and water (100 ml) at room temperature for two hours. The mixture is extracted with ether (2×50 ml) to afford the product as a yellow oil 4.5 g (90%). 1HNMR (DMSO-d6): delta (ppm) 1.03 (t, 3H), 2.92 (q, 2H), 5.38 (q, 2H) 7.56 (t, 1H), 7.74 (s, 1H), 7.92 (d, 1H), 7.95 (d, 2H), 8.06 (s, 1H), 8.12 (s, 1H).

The synthetic route of 766-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2007/4786; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 5003-71-4, 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. 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide, This compound has unique chemical properties. The synthetic route is as follows.

Triethylamine (30 mL) was added dropwise to 3-bromopropan-1-aminium bromide (10.84 g, 50 mmol) in DCM (50 mL). After 15 min stirring, di-tert-butyl dicarbonate (21.8 g, 100 mmol) in DCM (40 mL) was added dropwise to the solution for 1 h, and the resulting mixture was stirred for 2 days at room temperature. The resulting solution was washed with 1 N aqueous HCl, water × 2, saturated aqueous NaHCO3, and brine. The organic phase was dried with Na2SO4, and thes olvent was removed in vacuo to give tert-butyl (3-bromopropyl) carbamate (20.54 g, yield = 88%).

The chemical industry reduces the impact on the environment during synthesis 3-Bromopropan-1-amine hydrobromide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Qin, Huihuan; Li, Lingling; Li, Kun; Xiaoqi, Yu; Chinese Chemical Letters; (2019); p. 71 – 74;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1137142-58-5, 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. 1137142-58-5 name is 2-Bromoimidazo[2,1-b][1,3,4]thiadiazole, 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.

Intermediate 23; lmidazo[2,1-b][1,3,4]thiadiazol-2-yl-(4-methoxyphenyl)amine; A mixture of 2-bromo-imidazo[2,1-b][1 ,3,4]thiadiazole (1.0 g, 4.90 mmol) and p- anisidine (19.6 mmol, 2.41 g) in trifluoroethanol (12 mL) was heated under microwave irradiation at 170C for 1 hour. On cooling, the mixture was diluted with dichloromethane (10 mL) and purified by column chromatography (Biotage/Flash, silica, methanol:dichloromethane 0.2:9.8 to 1 :9). The residue obtained was triturated with diethylether and few drops of methanol to give imidazo[2,1-b][1 ,3,4]thiadiazol-2-yl-(4-methoxyphenyl)amine as a white solid (355 mg, 29% yield). 1H-NMR (300 MHz, CDCI3): delta 8.01 (s, 1 H), 7.55 (s, 1 H), 7.44 (d, J = 8.9, 2H), 7.22 (s, 1H), 6.90 (d, J = 8.8, 2H), 3.80 (s, 3H). MS (ES+) m/z 247 (M+H)+ (MW: 246.29).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromoimidazo[2,1-b][1,3,4]thiadiazole, and friends who are interested can also refer to it.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); WO2009/40552; (2009); A2;,
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

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

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

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

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

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

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