Category: bromides-buliding-blocks

Synthetic Route of 18599-22-9, A common heterocyclic compound, 18599-22-9, name is 4-Bromo-3,3,4,4-tetrafluorobut-1-ene, molecular formula is C4H3BrF4, 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.

General procedure: In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar, were added iodobenzene (3a, 0.40 mL, 3.6 mmol) and Cu2O (0.027 g, 0.18 mmol), and a DMF solution of 2-Zn (0.60 M, 1.0 mL, 0.6 mmol). The whole was heated up at 100 C and stirred at that temperature for 24 h. After cooling to room temperature, the resultant was filtered through a short pad of silica gel using hexane as an eluent. The filtrate was concentrated in vacuo to give the crude materials, which was purified by silica gel column chromatography using hexanes as an eluent, leading to the corresponding compound 4a (0.036 g, 0.17 mmol) in 29% isolated yield as a colorless oil.

The synthetic route of 18599-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tamamoto, Ken; Yamada, Shigeyuki; Konno, Tsutomu; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2375 – 2383;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 2924-09-6, name is 5-Bromo-2-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 2924-09-6, Computed Properties of C6H5BrFN

Example 25Synthesis of TRV 1 159TRV 1159 (4-(3-(benzylamino)-4-fluorophenyl)piperazin- 1 -yl)(phenyl)methanone [00164] Scheme for TRV 1 159[00165] 5-bromo-2-fluoroanile (0.500 g, 2.63 mmol) and benzaldehyde (0.27 mL, 2.63 mmol) were dissolved in DCM (8.8 mL) and then treated with NaBH(OAc)3 (0.837 g, 3.95 mmol) and AcOH (0.23 mL, 3.95 mmol). This mixture was stirred at room temperature under argon until complete by TLC. The reaction was quenched by the dropwise addition of IN NaOH (20 mL). This mixture was then extracted with EtOAc (3x 20 mL). The combined organic layers were washed with H2O, brine, dried (Na^SC^), filtered and concentrated to give 1.0 g of an oil. This crude oil was purified via flash chromatography (5 % EtOAc / hexane to give 0.6127 g (83 % yield) of the desired benzylamine. The benzyl amine (0.5032 g, 1.8 mmol), benzoylpiperazine hydrochloride (0.4897 g, 2.16 mmol) and NaOiBu (0.517 g, 5.38 mmol) were added to a tube. The tube was evacuated and flushed with argon for three cycles. Toluene (5.4 mL) and NMP (3.2 mL) were then added and the mixture was degassed with argon for 30 minutes. Pd2(dba)3 (0.033 g, 0.036 mmol) and BINAP (0.0448 g, 0.072 mmol) were then added, the tube was sealed and heated overnight at 100C. After cooling, the mixture was diluted with water and EtOAc. The aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed with H20, IN HC1 (2x), saturated NaHC03, H20 and brine before drying with Na2S0 . The material was filtered and concentrated under reduced pressure to give 1.3 g of crude brown oil. Initial purification via flash chromatography (45 % EtOAc / hexane) failed to separate the product from the minor by-product. A second chromatographic process (20 % EtOAc / hexane) was used to afford 0.1998 g (24 % yield) of TRV1159. NMR (500 MHz, CDC13) delta = 7.47-7.41 (m, 5H), 7.38-7.34 (m, 4H), 7.30-7.27 (m, 1H), 6.88 (dd, J = 1 1.5, 8.5 Hz, 1 H), 6.26 (dd, J = 7.5, 3.0 Hz, 1 H), 6.16 (dt, J = 8.5, 3.0 Hz, 1 H), 4.35 (s, 2H), 4.32 (br s, 1H), 3.89 (br s, 2H), 3.54 (br s, 2H), 3.09 (br s, 2H), 2.95 (br s, 2H). Example 26 Synthesis of TRV 1 158

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Reference:
Patent; TREVENTIS CORPORATION; REED, Mark, A.; YADAV, Arun; BANFIELD, Scott, C.; BARDEN, Christopher, J.; WO2012/119035; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 156682-52-9,Some common heterocyclic compound, 156682-52-9, name is 1,4-Dibromo-2,3-difluorobenzene, molecular formula is C6H2Br2F2, 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 4 (5 g, 18.1 mmol),1,4-dibromo-2,3-difluorobenzene (2.4 g, 9.0 mmol), Tetrakis (triphenylphosphine) palladium (0) (0.9 g, 0.9 mmol) Tetrahydrofuran (60 ml) and potassium carbonate 2M solution (20 ml) were added to a mixed solvent and refluxed for 24 hours.After completion of the reaction, the reaction solution was extracted with methylene chloride and methylene chloride / hexane mixed solvent was subjected to column chromatography with a developing solvent to obtain 4.3 g of intermediate 5.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Dibromo-2,3-difluorobenzene, its application will become more common.

Reference:
Patent; LG Chem, Ltd.; Dankook University Cheonan Campus Industry-Academic Cooperation Foundation; Gu Gi-dong; Lee Gi-gon; Keum Su-jeong; Kim Gong-gyeom; Lee U-cheol; Lee Chil-won; Cha Jae-ryeong; Joo Yun-seok; (37 pag.)KR2019/109846; (2019); 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. 22034-13-5, name is 4-Bromobenzo[c][1,2,5]thiadiazole, A new synthetic method of this compound is introduced below., Product Details of 22034-13-5

A mixture of 2,7-bis-boronic acid pinacol ester-4-hexylcarbazole-9,9-diarylfluorene (0.2 g, 0.24 mmol, 1 equiv), 4-bromo-2,1,3-thiadiazole (0.206 g, 1 mmol, 4 equiv) were dissolved in 15 ml of a dry bubbling packed with tetrahydrofuran in N2, 5 ml of potassium carbonate aqueous solution (2 mol / L), followed by the addition of 40 mg of palladium catalyst tetraphenylphenylphosphine The reaction mixture was heated at 85 ¡ã C for 24 h and extracted with methylene chloride. After drying, the mixture was purified by rotary distillation using petroleum ether: dichloromethane = 4: 1 silica gel to give a powdery solid in 68percent

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; Nanjing Tech University; Han Yamin; Bai Lubing; Lin Jinyi; (12 pag.)CN106967056; (2017); A;,
Bromide – Wikipedia,
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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. 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, A new synthetic method of this compound is introduced below., SDS of cas: 33070-32-5

40 g (0.169 mol) of the 5-bromo-2,2-difluorobenzodioxole prepared in Example 1 and 108 g (121.5 ml) of tetrahydrofuran were placed in a 1 L reaction flask, and the mixture was stirred under a nitrogen atmosphere to cool the system to -10 C, control system temperature -10 ~ 0 C, A solution of 104 g (0.202 mol) of 20% isopropylmagnesium chloride in tetrahydrofuran was added dropwise to the system to control the dropping rate, and the dropwise addition was completed in about 3 hours. After the completion of the dropwise addition, the reaction was kept for 2 hours. The temperature was further lowered to -25 C, and 18.5 g (0.253 mol) of N,N-dimethylformamide was added dropwise, and the mixture was kept for 2 hours. Quenched by adding 200 ml of saturated ammonium chloride solution, adding 15% hydrochloric acid to adjust the pH value of 5-6, adding 250 g of dichloromethane to extract, layering, transfer the lower organic phase to 500 ml reaction flask at 60 C, and concentrate under reduced pressure until no fraction was obtained to give the intermediate product 2,2-difluoro-1,3-benzodioxan-5-carbaldehyde 28.6 g (0.153 mol). The system was cooled to 20-30 C, and 180 g of absolute ethanol was added.Under nitrogen protection, stirring was started, and 2.55 g (0.067 mol) of sodium borohydride was slowly added to the system in portions, and the addition was completed in about 3 hours. After the addition of heat for 30 min, the reaction was quenched by adding 800 g of water, and then extracted with 205 g of dichloromethane, and the mixture was allowed to stand for separation. The lower organic layer was evaporated and concentrated at 60 C, -0.08Mpa (G) to no fraction, and obtain the 2,2-fluorobenzo[d][1,3]dioxo-5-yl)methanol 25.7g, The purity of the gas was determined by gas chromatography to be 96% (0.131 mol, yield 77.7%, based on 5-bromo-2,2-difluorobenzodioxole)

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; Fuxin Da Deli Chemical Co., Ltd.; Nie Qiang; Zhang Jinsheng; Jiang Shan; Jia Yitong; (9 pag.)CN109503544; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, 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 337915-79-4, COA of Formula: C7H9BrN2

Example 30 4- ( (4-Chlorobenzyl) oxy) -1- (2-isopropyl-l-methyl-lH- benzimidazol-6-yl) pyridin-2 (1H) -one A) 6-Bromo-2-isopropy1-1-methyl-lH-benzimidazole To a solution of 5-bromo-Nx-methylbenzene-l, 2-diamine. (122 mg) and isobutyric acid (0.056 ml) in DMF (2 ml) was added HATU (242 mg) at room temperature. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. After being stirred, N, N-diisopropylethylamine (0.311 ml) was added to the reaction mixture. The mixture was stirred at room temperature for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgS04 and concentrated in vacuo. The resulting residue was stirred in AcOH (2.00 ml) at 90C for 1 h and at room temperature overnight. The mixture was quenched with saturated NaHCC>3 solution at room temperature and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSC>4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (119 mg) as a pale yellow solid. MS (ESI+) : [M+H]+ 255.0.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KASAI, Shizuo; IGAWA, Hideyuki; TAKAHASHI, Masashi; MAEKAWA, Tsuyoshi; KAKEGAWA, Keiko; YASUMA, Tsuneo; KINA, Asato; AIDA, Jumpei; KHAMRAI, Uttam; KUNDU, Mrinalkanti; WO2013/105676; (2013); 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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, A new synthetic method of this compound is introduced below., Safety of 1,3-Dibromo-5-fluorobenzene

Example 6 a) 20.0 g (78.8 mmol) 1,3-dibromo-5-fluoro-benzene, 16.3 g (78.8 mmol) 6H-benzimidazolo[1,2-a]benzimidazole and 43.5 g (0.315 mmol) potassium carbonate in 200 ml DMF are stirred for 17 h at 170 C. The reaction mixture is filtered hot and the precipitate from the mother liquor is filtered after cooling. The product is washed with water and ethanol and decocted with diethyl ether and ethanol. Yield 21.2 g (61%).1H NMR (400 MHz, THF-d8): delta 8.21-8.26 (m, 4H), 7.98-7.8.00 (m, 1H), 7.68-7.73 (m, 2H), 7.31-7.49 (m, 4H).

The synthetic route of 1435-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; US2012/241681; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 699-03-6, 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. 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of tetrafluoropyridazine 1, DIPEA, amine and THF (10 mL) was stirred for the required time under an atmosphere of nitrogen. The mixture was evaporated to dryness in vacuo, partitioned between ethyl acetate (20 mL) and water (20 mL), the phases were separated and the aqueous phase was extracted further by ethyl acetate (3 x 20 mL). The combined organic phases were dried (MgSO4) and evaporated in vacuo. Purification by column chromatography or HPLC on silica gel using cyclohexane and ethyl acetate as eluent gave the pure product.

The synthetic route of 1-(4-Bromophenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pattison, Graham; Sandford, Graham; Wilson, Ian; Yufit, Dmitrii S.; Howard, Judith A.K.; Christopher, John A.; Miller, David D.; Tetrahedron; vol. 73; 5; (2017); p. 437 – 454;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 18648-66-3, name is 2-(4-Bromophenyl)-1,1-diphenylethylene, molecular formula is C20H15Br, 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. Formula: C20H15Br

(1) Synthesis of 2-(2-biphenylyl)-9,10-bis(4-(2,2-diphenylvinyl)phenyl)-9,10-dihydroxy-9,10-dihydro anthracene; [Compound (B1-0)]; Under an atmospheric argon gas flow, 4-(2,2-diphenylvinyl)-1-bromobenzene in an amount of 9.8 g (29 mmol, 3 eq) was dissolved into a mixed solvent of anhydrous toluene in an amount of 45 milliliter and anhydrous THF in an amount of 45 milliliter, followed by cooling down to the temperature of – 20 C by means of dry ice / methanol bath. Adding hexane solution of n-butyllithium in an amount of 19 milliliter (1.59 mol/litter, 30 mmol; 1.04 eq), the resultant solution was stirred at the temperature of -20 C for 1 hour. Into the resultant solution, 2-(2-biphenylyl)-9,10-anthraquinone [Compound (A)] in an amount of 3.5 g (9.7 mmol) was added and after stirring at the room temperature for 2 hours, it was stood alone for a night. The resultant reaction mixture was deactivated with the use of saturated ammonium chloride aqueous solution in an amount of 50 milliliter, and the resultant solid was separated. The solid was washed use of the mixed solvent of hexane : dichloromethane = 1:1 (capacity ratio) and as a result, 5.0 g of white solid compound was obtained (yield: 59 %). The white solid was identified as the Compound (B1-0) in accordance with 1H-NMR. The measurement results of 1 H-NMR are shown as the following: 1H-NMR (CDCl3, TMS) delta 2.17 (1H, s), 2.66 (1H, s), 6.21 (2H, d, J=8Hz), 6.51 (2H, d, J=8Hz), 6.55 (4H, s), 6.80 (2H, d, J=4Hz), 7.0-7.4 (3H, m), 7.6-7.7 (3H, m)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18648-66-3, its application will become more common.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; EP1695952; (2006); 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. 556-96-7, name is 1-Bromo-3,5-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H9Br

2-bromo-3,5-dimethylbenzene 15a (1.06 g, 5.70 mmol), bis(pinacolato)diboron (2.0 g, 8.60 mmol),1,1 ‘-bis (diphenylphosphino) ferrocene] dichloropalladium (210 mg, 0.20 mmol) and potassium acetate (1.40 g, 14.30 mmol) was dissolved in 20 mL of ethylene glycol dimethyl ether and heated to reflux for 3 hours. Filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using eluent system B to give the title product, 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 15b (538 mg, yellow oil), yield: 42.1%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 556-96-7.

Reference:
Patent; SHANGHAI HENGRUI PHARM CO LTD; JIANGSU HENGRUI MEDICINE CO LTD; Lyu, HEJUN; DONG, QING; FEI, HONGBO; JIANG, HONGJIAN; SONG, PENG; (114 pag.)CN103030646; (2016); B;,
Bromide – Wikipedia,
bromide – Wiktionary