Category: bromides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 53965-69-8, name is 4-Bromo-2,3,5,6-tetramethylaniline, 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 53965-69-8, Application In Synthesis of 4-Bromo-2,3,5,6-tetramethylaniline

n the S104, the third intermediate (2.25 g, 5 mmol), 4-bromo-2,3,5,6-tetramethylaniline (1.39 g, 6 mmol) in argon was added to a 250 mL two-necked flask. In a gas atmosphere, 100 mL of acetone with water and oxygen removed in advance was injected, and the reaction was performed at 60 C for 24 hours. The reaction solution was poured into 200 mL of ice water, and extracted with dichloromethane three times. The organic phases were combined, and the mixture was separated into silica gel by column chromatography (dichloromethane: n-hexane, v: v, 1: 1) to obtain 2.41 g of a white powder. The yield is 80%. MS (EI) m / z: [M] +: 604.13. The theoretical relative molecular mass of the first reactant is 604.25.

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; Wuhan Hua Xing Optoelectric Semiconductor Display Co., Ltd.; Luo Jiajia; (18 pag.)CN110511223; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 937046-98-5, 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. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred suspension of Intermediate B (523 mg, 2.46 mmol), terf-butyl 4-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1 (2H)-carboxylate (Eastwood, P. R. Tetrahedron Lett. 2000, 41, 3705) (950 mg, 3.07 mmol), and 1,1′- bis(diphenylphosphino)-ferrocene]dichloro palladium(ll)-complex with dichloromethane (180 mg, 0.25 mmol) in degassed DME (18 mL) was added aqueous Na2CO3 solution (2 M, 3.7 mL). The reaction was heated (80 0C) for 17 h and then cooled to rt. The mixture was partitioned between ethyl acetate (50 mL) and H2O (50 mL). The layers were separated and the organic layer was washed with brine (25 mL), dried (Na2SO4), and concentrated to dryness. The crude residue was purified by ISCO chromatography using a gradient of 50 to 75% ethyl acetate in hexanes to afford 584 mg (75%) of the desired product as an off-white solid, which contained trace impurities. 1H NMR (300 MHz, DMSO-d6) delta 7.85 (s, 1 H), 7.68 (br s, 2 H), 6.97 (br s, 1 H)1 6.87 (d, 1 H), 6.66 (d, 1H), 4.07-4.00 (m, 2 H), 3.53 (t, 2 H), 2.56-2.50 (m, 2 H), 1.42 (s, 9 H); ES-MS m/z 316.1 [MH-H]+, HPLC RT (min) 2.31.

The chemical industry reduces the impact on the environment during synthesis 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/56170; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 58971-11-2,Some common heterocyclic compound, 58971-11-2, name is 3-Bromophenethylamine, molecular formula is C8H10BrN, 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 116: 5-(1 -cyclohexyl-5-(methoxymethyl)-1 H-pyrazol-4-yl)-3-(1 ,2,3,4- tetrahydroisoquinolin-6-yl)-1 ,2,4-oxadiazoleStep 1: N-(3-bromophenethyl)-2,2,2-trifluoroacetamide; To a solution of 3-bromophenethylamine (2.46 g; 12.3 mmol) in DCM (15 mL) was added diisopropylamine (3.18 g; 24.6 mmol) and trifluoroacetic anhydride (2.84 g; 13.5 mmol) and the mixture was stirred for 16 hours. The solvent was removed in vacuo and the residue was triturated with DCM (1 mL) and petrol (10 mL) to give the title compound (2.57 g; 70 %) as a pale yellow solid. 1H NMR (CDCI3, 400MHz) delta 7.40 (1 H, d, J = 8.0 Hz), 7.36 (1 H, s), 7.21 (1 H, t, J = 7.8 Hz), 7.12 (1 H, d, J = 7.7 Hz), 6.37 (1 H, br s), 3.65-3.57 (2 H, m), 2.87 (2 H, t, J = 7.1 Hz).

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

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; BAKER-GLENN, Charles; BLACKABY, Wesley; KNIGHT, Chris; WO2010/142628; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

7051-34-5, name is (Bromomethyl)cyclopropane, 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. Application In Synthesis of (Bromomethyl)cyclopropane

In a round bottom flask,1 mmol of p-hydroxybenzaldehyde was added,20mL acetone dissolved,Stir evenly,3.0 mmol of potassium carbonate was added,A mixture of 1.0 equiv haloalkanes (bromomethylcyclopropane,1-bromo-3-methyl-2-butene,Bromo isobutane) in acetone solution 5 mL,The reaction was then allowed to reflux at an oil bath temperature of 65 C,The time and temperature of the reaction can be adjusted according to TLC detection,In order to carry out the reaction more thoroughly,Can be added in the middle of the reaction of 0.5equiv potassium carbonate,After the end of the reaction,First, the reaction solution was filtered under reduced pressure,The acetone solvent in the filtrate was distilled off under reduced pressure,The resulting mixture was then dissolved in methanol,Can be dissolved,Add 10 mL of the appropriate amount of saturated aqueous solution of potassium carbonate,Stirred at room temperature for 30 min,By potassium carbonate and unreacted 4-hydroxy acid esterification reaction,And then extracted with methylene chloride and saturated aqueous sodium chloride into the aqueous phase,According to the organic phase color to determine the number of extraction,Usually 3 times for the best,It is possible to remove the reaction substrate which does not participate in the reaction,The organic phase was dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain an etherified product having a high purity.

The synthetic route of 7051-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TONGJI UNIVERSITY; WANG, HONGBING; WANG, ZHUO; (17 pag.)CN105967992; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, 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. Computed Properties of C6H11Br

General procedure: General Procedure: In a 10 mL Schlenk tube were placed CoBr2 (0.3 M in THF, 0.10 mL, 0.030mmol), 1,3-diisopropylbenzimidazolium bromide (L2, 8.5 mg, 0.030 mmol), 2-alkenylpyridine(0.30 mmol), alkyl chloride (0.45 mmol), N,N,N,?N?-tetramethylethylenediamine (90 muL, 0.60mmol) and THF (0.28 mL). To the mixture was added a THF solution of tBuCH2MgBr (0.96 M,0.63 mL, 0.60 mmol) dropwise at 0 C. The resulting mixture was stirred at room temperature for12 h, and then quenched by the addition water (1.0 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3 x 3 mL). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by silicagel chromatography to afford the alkylation product.

The synthetic route of (Bromomethyl)cyclopentane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yamakawa, Takeshi; Seto, Yuan Wah; Yoshikai, Naohiko; Synlett; vol. 26; 3; (2015); p. 340 – 344;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 51554-93-9, 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. 51554-93-9 name is 1-Bromo-4-octylbenzene, 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.

Pd(OAc)2 (0.115 mg, 0.514 mumol), and S-Phos (0.211 mg, 0.514 mumol) were added to a suspension of K2CO3 (17.75 mg, 0.128 mmol), 1-bromo-4-octylbenzene (6.12 mul, 0.026 mmol), tert-butyl 4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate (10 mg, 0.026 mmol), in acetonitrile/water (1.5:1). The suspension was degassed for 5 min and then refluxed for 6 h. The reaction mixture was extracted with EtOAc, washed with brine, dried with MgSO4 and filtered. After evaporation of the organic solvent under reduced pressure, the resulting residue was purified by column chromatography over silica gel (100% hexanes to 70/30 hexanes/EtOAc) to provide a yellow oil (93% yield). 1H NMR (500 MHz, CDCl3) delta 7.90 (d, J = 8.3 Hz, 2H), 7.58-7.50 (m, 1H), 7.23 (d, J = 7.6 Hz, 2H), 7.10 (d, J = 7.6 Hz, 1H), 6.57 (d, J = 8.5 Hz, 1H), 3.64-3.55 (m, 8H), 2.67-2.60 (m, 2H), 1.67-1.57 (m, 2H), 1.49 (s, 9H), 1.36-1.24 (m, 8H), 0.87 (t, J = 6.8 Hz, 3H); 13C NMR (126 MHz, CDCl3) delta 158.9, 155.5, 155.0, 143.8, 138.3, 137.3, 128.7, 126.7, 109.9, 105.4, 80.0, 45.2, 35.8, 32.0, 31.5, 29.6, 29.4, 29.3, 28.5, 22.8, 14.2; HRMS (ESI+) m/z calcd for C28H41N3O2 [M+H]+ 452.3199, found 452.3605.The Boc-protected amine was dissolved in 10 mL methanol and HCl (g) was bubbled through the solution for one minute. After evaporation of the methanol, diethyl ether was added and the solid filtered. It was washed with cold diethyl ether to yield the title compound as orange oil (92% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-octylbenzene, and friends who are interested can also refer to it.

Reference:
Article; Raje, Mithun R.; Knott, Kenneth; Kharel, Yugesh; Bissel, Philippe; Lynch, Kevin R.; Santos, Webster L.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 183 – 194;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, 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. Computed Properties of C6H4BrF2N

4-bromo-2,6-difluoroaniline (31.05 g, 0.15 mol)N-isopropylacetamide (30.3 g, 0.30 mmol),Phosphorus oxychloride (20.9 mL, 0.225 mol) was added successively to anhydrous toluene.Triethylamine (31.3 mL, 0.225 mol) was slowly added dropwise to the reaction flask in a constant pressure funnel under ice-Keep the internal temperature less than 60 C.The reaction flask was transferred to an oil bath and heated to solvent reflux.After 2 hours the reaction flask was cooled to room temperature,Slowly poured into a 300 g ice-water mixture,Add 300 ml of ethyl acetate,After mixing well,The aqueous layer was again extracted with 200 ml of ethyl acetate,Combined organic layer,After washing with saturated brine, dried over anhydrous sodium sulfate,Concentrated under reduced pressure to obtain a pale yellow solid,Add 100 ml of petroleum ether beating for 10 minutes,The compound of formula IX-1 (28.0 g) was filtered off under reduced pressure,As an off-white solid (yield 92.3%).

The synthetic route of 4-Bromo-2,6-difluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Zhang, Yinsheng; Liu, Yingshuai; Li, Li; Miao, Lei; Xu, Tongjie; Liu, Haiyan; Ma, Xueqin; Yu, Sen; Xu, Hongjiang; (49 pag.)CN106467517; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 10546-67-5, 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. 10546-67-5, name is 2,6-Dibromo-4-(tert-butyl)aniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The aniline (75 g, 67 mol) was dissolved in DMF (37 mL), NBS added (25 grams; 142 mrnol) and the solution stirred at RT overnight. The solution was diluted with aqueous NaOH (I N, 370 mL) followed by aqueous/EtOAc work-up to afford the titled compound. The crude oil was dissolved in DMF (24 mL), added dropwise to a 70 0C solution of isoamyl nitrite (1 1.8 g, 101 mmol) in DMF (24 mL) and stirred for 30 minutes. The solution was cooled to RT, diluted with water (700 mL), acidified with AcOH, followed by aqueous/EtOAc work-up and silica gel chromatography (hexanes, neat) to afford the titled compound.

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, 2,6-Dibromo-4-(tert-butyl)aniline, other downstream synthetic routes, hurry up and to see.

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

Reference of 627871-16-3,Some common heterocyclic compound, 627871-16-3, name is 5-Bromo-4-fluoro-2-methylaniline, molecular formula is C7H7BrFN, 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.

To a solution of vinylidene chloride (127 ml), tert-butyl nitrite (19 ml) and copper(ll)chloride (18.4 g) in acetonitrile (150 ml) is added a solution of 5-bromo-4-fluoro-2-methyl-phenylamine (Bioorganic & Medicinal Chemistry Letters (2006), 16(2), 457-460) (21.5 g) in acetonitrile (100 ml) dropwise below 200C. The reaction mixture is stirred at room temperature for 48 hours, poured on diluted HCI and extracted with fert-butyl methyl ether (3x). The combined organic layers are washed with brine, dried over sodium sulfate and concentrated. The residue is purified by chromatography on silica gel (ethyl acetate/cyclohexane 1 :4). Yield: 29.20 g of 1-bromo-2-fluoro- 4-methyl-5-(2,2,2-trichloro-ethyl)-benzene as an oil.1H-NMR (CDCI3): 2.42 (s, 3H), 3.93 (s, 2H), 7.00 (d, 3J(H,F)=9.2Hz, 1 H), 7.69 (d, 4J(H,F)=7.0Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-4-fluoro-2-methylaniline, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; ZAMBACH, Werner; HUETER, Ottmar Franz; WENGER, Jean; GOEGHOVA, Marcela; PITTERNA, Thomas; MAIENFISCH, Peter; JEANMART, Stephane Andre Marie; MUEHLEBACH, Michel; WO2010/52161; (2010); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, 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. Product Details of 129316-09-2

(4) (Suzuki) by Suzuki coupling reaction to obtain the final product f: the 9 – benzene anthracene -10 borate 10 mmol, 1, 3 – dibromo – 4, 6 – dihydro -5 – tert butyl 2 mmol, four (triphenylphosphine) palladium 0.4 mmol, toluene 80 ml, ethanol 20 ml, K2CO344 MmoL (for 20 ml distilled water into the solution), is added to the reaction bottle, then the system vacuum, in 110 C under the protection of nitrogen reflux 24 hours. After the completion of the reaction, methanol hot washing and filtering, toluene recrystallization, distillation to obtain the final product f. Yield 66%.

The synthetic route of 129316-09-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shaanxi Normal University; Hu Jianyong; Zhang Jiali; Zhao Zhen; Duan Xuewei; (18 pag.)CN109678645; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary