Category: bromides-buliding-blocks

Electric Literature of 21524-34-5,Some common heterocyclic compound, 21524-34-5, name is 2-Bromo-1,3,5-triisopropylbenzene, molecular formula is C15H23Br, 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: An oven-dried, resealable Schlenk tube containing a stirbar was charged with aryl halide (1.0 mmol), ketone (1.1 mmol), potassium tert-butoxide (1.5 mmol), and 1 mol % catalyst, and backfilled with nitrogen. Toluene (1.5 mL) was sequentially injected, and the mixture was stirred in an oil bath at reflux temperature for the time specified. After the reaction was completed, the reaction mixture was filtered by chromatographed on silica gel and washed with EtOAc. The filtrate was dried over MgSO4 and filtered before the solvent was removed on a rotary evaporator. The pure product was obtained by preparative TLC and the yield was calculated based on ArX (the purified products were identified by comparison of melting points with the literature data or by 1H NMR and 13C NMR spectra. New compounds were determined by HRMS spectra).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1,3,5-triisopropylbenzene, its application will become more common.

Reference:
Article; Zhang, Jinli; Yang, Xueqian; Cui, Xiuling; Wu, Yangjie; Tetrahedron; vol. 67; 45; (2011); p. 8800 – 8807;,
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. 10269-01-9, name is (3-Bromophenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 10269-01-9

General procedure: A mixture of 0.55mmol of 8-bromo-7-(2-bromoethyl)theophylline 7a or 8-bromo-7-(3-chloropropyl)theophylline 7b or 8-bromo-7-(4-bromobutyl)theophylline 7c, 1.1mmol of appropriate aromatic amine, 1,6 mmol of TEBA and 1.00ml of propanol was heated in closed vessels in microwave oven (300 Watt, Power Max Off, 160C, 10bar) for 1h. The solvent was removed and the residue was treated with ethanol. The products were purified by crystallization from ethanol or flash column chromatography over silica gel with CH2Cl2 : MeOH (100 : 0 to 80 : 20). The precipitate was filtered off and dried.

According to the analysis of related databases, 10269-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Za?uski, Micha?; Schabikowski, Jakub; Schlenk, Miriam; Olejarz-Maciej, Agnieszka; Kubas, Bart?omiej; Karcz, Tadeusz; Kuder, Kamil; Latacz, Gniewomir; Zygmunt, Ma?gorzata; Synak, David; Hinz, Sonja; Mueller, Christa E.; Kie?-Kononowicz, Katarzyna; Bioorganic and Medicinal Chemistry; vol. 27; 7; (2019); p. 1195 – 1210;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 16657-07-1,Some common heterocyclic compound, 16657-07-1, name is 7-Bromo-1H-indene, molecular formula is C9H7Br, 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.

(1) Synthesis of 7-isopropylindene Using a 300 ml three-necked flask as the reactor, under a nitrogen stream, 1.36 g (2.57 millimoles) of [1,2-bis (diphenylphosphino)ethane]dichloronickel(II) was dissolved in 20 ml of tetrahydrofuran. To this suspension there was added a solution of 10 g (51.30 millimoles) of 7-bromoindene in 100 ml of tetrahydrofuran, prepared based on the method described in J. Org. Chem. 49, 4226-4237(1984). After dropwise addition of 51 ml (102.60 millimoles) of isopropylmagnesium bromide (2N) to the mixed solution while cooling on ice, the mixture was heated to reflux for 20 hours. After reflux, hydrolysis was performed with a saturated aqueous solution of ammonium chloride, distilled water was added, extraction was performed several times with diethyl ether, and then the extract was washed once with saturated saline and dried over anhydrous magnesium sulfate. After drying, the magnesium sulfate was filtered off and the solvent was purified with a silica gel column to obtain 7.14 g of 7-isopropylindene as a yellow oil (88% yield).

The synthetic route of 16657-07-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chisso Petrochemical Corporation; US2003/149200; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

50548-45-3, name is 1-Bromodibenzo[b,d]furan, 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. Safety of 1-Bromodibenzo[b,d]furan

(4) In a 1L reaction flask, add intermediate c (51.65 g, 100 mmol), 9-phenyl-9H-carbazole-2-amine (25.83 g, 100 mmol), and tris (dibenzylideneacetone) diamine. Palladium (2.75g, 3mmol), tri-tert-butylphosphine (1.21g, 6mmol), sodium tert-butoxide (19.22g, 200mmol), 500ml of toluene, heated to 110 C for 12h under a nitrogen atmosphere, and monitored by liquid phase After the reaction is completed, the temperature is lowered, 1-bromodibenzofuran (24.71 g, 100 mmol) is added, the temperature is raised to 110 C and the reaction is continued for 8 hours. The reaction is monitored by liquid phase, cooled to room temperature, washed with water, filtered, ethyl acetate, dried, 54.18 g of intermediate e can be obtained with a yield of 63%.

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

Reference:
Patent; Wuhan Shang Sai Optoelectric Technology Co., Ltd.; Mu Guangyuan; Zhuang Shaoqing; Ren Chunting; (31 pag.)CN110372570; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, 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 16518-62-0, Recommanded Product: 16518-62-0

Step A: bis-(3-dimethylaminophenyl)amine Under dinitrogen atmosphere, 1 equivalent of 3-bromo-N,N-dimethylaniline (1 g), 1.5 equivalent of sodium tert-butylate (0.721 g), 0.1 equivalent of Pd(dba)2 (0.288 g), 0.12 equivalent of dppf (0.555 g) and 20 mL of toluene are introduced into a flask. The flask is fitted with a PTFE septum and 1.2 equivalent of N,N-dimethylbenzene-1,3-diamine (0.817 g) is added thereto using a syringe. The reaction medium is heated at 90¡ã C. for 12 hours, thereafter is cooled to room temperature and concentrated under reduced pressure. The product is purified by flash chromatography using a gradient of 5percent to 12percent of ethyl acetate in hexane (Rf: 0.33) to give 0.963 g of the expected product with a yield of 75percent.NMR 1H: (CDCl3) 7.13 (t, 2H), 6.5 (d, 2H), 6.49 (d, 2H), 6.38-6.36 (m, 2H), 5.68 (s large, 1H), 2.95 (s, 12H).MS (M+1): 256

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, 3-Bromo-N,N-dimethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMA HYDRO DEVELOPMENT – P.H.D.; US2010/204215; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 58971-11-2, These common heterocyclic compound, 58971-11-2, name is 3-Bromophenethylamine, 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.

A mixture of intermediate I-60 (8.0 g, 40 mmol, 1.0 eq) and 2,6-lutidine(4.8 mL, 41 mmol, 1.03 eq) in dry dichloromethane (160 mL) was cooled to 0 C. and neat TFAA (5.6 mL, 39.6 mmol, 0.99 eq) was added drop wise. The reaction mixture was warmed to room temperature and stirred for 16 hours. Water (150 mL) was added, the aqueous layer was extracted with dichloromethane and the combined organic layers were washed with aqueous HCl (1.0 M in water) and a saturated aqueous solution of NaHCO3. The combined organic layers were dried over anhydrous Na2SO4, the solids were removed by filtration and the filtrate was concentrated by evaporation to give intermediate I-61 (11 g, 92%). 1H-NMR (400 MHz, CDCl3) delta: delta 7.40 (d, 1H, J=8.0 Hz), 7.35 (t, 1H, J=1.6 Hz), 7.20 (t, 1H, J=7.6 Hz), 7.12 (d, 1H, J=8.0 Hz), 6.55 (brs, 1H), 3.59 (q, 2H, J1=6.4 Hz, J2=13.2 Hz), 2.86 (t, 2H, J=6.8 Hz). MS (ESI): m/z 296 (M+H+).

Statistics shows that 3-Bromophenethylamine is playing an increasingly important role. we look forward to future research findings about 58971-11-2.

Reference:
Patent; Chytil, Milan; Engel, Sharon R.; Fang, Qun Kevin; Spear, Kerry L.; US2010/204214; (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. 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3BrN2O

5-Brorno-2,l,3-benzoxadiazole (5.5 g, 27.6 mmol)), potassium vinylfluoroborate (7.40 g, 55.3 mmol), and PdC12(dppi>;CH2C12Adduct (1.088 g, 1.332 mmol) were suspended in ethanol (75 ml) then added TEA (7.70 ml, 55.3 mmol). The reaction mixture was then degassed and heated to reflux for 3hrs. The reaction was diluted with ethyl acetate and washed with brine. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was purified through a 330g ISCO Redi-Sep silica gel plug and eluted with 20%ETOAc/hexane to yield 5- ethenyl-2 , 1 , 3 -benzoxadiazole.1H-NMR (600 MHz5 CDCl3): delta ppm 7.81(d, J=9.3 Hz, IH), 7.66 (s, IH), 7.63 (d, J-9.3 Hz, IHX 6.35 (d, J=10.9 Hz, 0.5H), 6.80 (d, J-10.9 Hz, 0.5H)s 5.94 (d. J-17.5 Hz, IH)5 5.55 (d, J= H Hz5 IH).

According to the analysis of related databases, 51376-06-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; PASTERNAK, Alexander; SHAHRIPOUR, Aurash; TANG, Haifeng; TEUMELSAN, Nardos, H.; YANG, Lihu; ZHU, Yuping; WALSH, Shawn, P.; WO2010/129379; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 24358-62-1, 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. 24358-62-1 name is 1-(4-Bromophenyl)ethylamine, 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 solution of di-tert-butyl dicarbonate (10.9 g, 50 mmol) in CH2Cl2 (50 ml) was added dropwise to an ice-cooled solution of 4-bromo-alpha-methylbenzylamine (10 g, 50 mmol) in CH2Cl2 (50 ml). After the mixture was stirred at room temperature for 30 min, the solvent was removed under reduced pressure which left a white solid. The mixture of this material, phenyl boronic acid (7.32 g, 60 mmol) and potassium carbonate(27.6 g, 200 mmol) in dioxane (300 ml) and water(120 ml) was deoxygenated, and then Pd(dppf)Cl2 (4.08 g, 5 mmol)was added. The resulting mix was heated under argon at reflux for 18 h. Catalyst was removed by filtration and the filtrate was concentrated, the residue was taken into EtOAc and washed with brine, dried (MgSO4) and concentrated. This material was purified by silica gel chromatography (330 g Redisep column, silica, 40 um, 60 , 100 mL/min, A: hexane, B: ethyl acetate, B: 2% for 2 min, 8% for 30 min, detection at 254 nm) to give 7.09 g (48%) of the title compound as a white solid. MS(ES) m/e (M-C4H8+)=242.0

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

Reference:
Patent; Goodman, Krista B.; Neeb, Michael J.; Sehon, Clark A.; Viet, Andrew Q.; Wang, Gren Z.; US2008/21023; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1000994-95-5, 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. 1000994-95-5, name is 1-Bromo-4-(1,1-difluoroethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Step 4:To a mixture of compound 5b4 (210 mg, 0.95 mmol) in DMF (6.0 mL) is added bis(pinacolato)diboron (265 mg, 1.045 mmol) and KOAc (205 mg, 2.09 mmol). Argon is passed through the mixture for 5 minutes and PdCI2(dppf)-CH2CI2 (77.6 mg, 0.095 mmol) is added. Argon is passed through the mixture for 3 minutes further and the mixture is allowed to react at 80C overnight. The mixture is extracted with EtOAc and the extract is washed with brine, dried (MgSO4), filtered through Celite and concentrated to provide boronic acid 5b5.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-(1,1-difluoroethyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2007/131350; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 153505-37-4, These common heterocyclic compound, 153505-37-4, name is 4-Bromo-5-fluorobenzene-1,2-diamine, 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.

To a solution of 4-bromo-5-fluorobenzene-1,2-diamine (4.50 g, 21.95 mmol), (S)-2-((tert-butoxycarbonyl)amino)-3 ,3-dimethylbutanoic acid (5.08 g, 21.95 mmol), DIPEA (3.83 mL, 21.95 mmol) in CH2C12 (200 mL) at 0 C was added HATU (8.35 g, 21.95 mmol). The reaction mixture was stirred for 18 h at RT. After which, water (500 mL) was added into the reaction mixture and extracted with ethyl acetate (3 x100 mL). The organic layer was washed with brine, dried (Na2SO4) and concentrated to afford Bla and/or ite regioisomer (10.0 g) as brown liquid. Crude was taken fornext step without further purification. LC/MS: Anal. Calcd. for [M+Hj mz C17H26BrFN3O3: 420.11; found 420.1.

The synthetic route of 153505-37-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; FRENNESSON, David B.; HEWAWASAM, Piyasena; LOPEZ, Omar D.; NGUYEN, Van N.; SAULNIER, Mark G.; TU, Yong; WANG, Alan Xiangdong; WANG, Gan; XU, Ningning; NIMJE, Roshan Yadavrao; RAHAMAN, Hasibur; GUPTA, Samayamunthula Venkata Satya Arun Kumar; MEANWELL, Nicholas A.; BELEMA, Makonen; (107 pag.)WO2017/23631; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary