Tag: M.W=200-300

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

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

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

Application of 2635-13-4,Some common heterocyclic compound, 2635-13-4, name is 5-Bromobenzo[d][1,3]dioxole, molecular formula is C7H5BrO2, 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 screw cap vial were added Pd(PPh3)2Cl2 (58.3 mg, 81.4 mumol), CuI (31.6 mg, 163 mumol),anhydrous DMF (0.33 mL), 4-bromo-1,2-(methylenedioxy)benzene (10d) (200 muL, 1.63 mmol)and Et3N (2.28 mL, 16.4 mmol) at rt. The solution was bubbled with argon gas for 5 min toremove the dissolved gases. Then, trimethylsilylethyne (350 muL, 2.44 mmol) was added, andthe reaction mixture was stirred at 90 C for 24 h. Upon completion of the reaction, the reaction mixture was concentrated by rotary evaporation. Purification by column chromatography(hexanes) yielded 11d (153 mg, 43%) as a brown liquid.

The synthetic route of 2635-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jeong, Yunkyung; Lee, Jooyeon; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 24; 9; (2016); p. 2114 – 2124;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 101417-40-7, name is 4-(Bromomethyl)benzo[d][1,3]dioxole, 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 101417-40-7, Quality Control of 4-(Bromomethyl)benzo[d][1,3]dioxole

7.5 g (0.033 mol) of 2,3-dimethoxymethylene benzyl bromide,4.5 g (0.036 mol) of m-hydroxybenzaldehyde and 13.5 g (0.099 mol) of potassium carbonate were dissolved in 80 ml of DMF.The reaction was stirred overnight at 40C. After the reaction was stopped, it was filtered after the temperature was lowered to room temperature.An equal volume of water and ethyl acetate were added to the filtrate and the layers were separated. The aqueous phase was extracted twice with ethyl acetate.The organic phases were combined and washed in the order of saturated sodium bicarbonate solution-water-saturated brine.Anhydrous sodium sulfate was dried for 8 h. The desiccant was filtered off, the solvent was evaporated under reduced pressure, and the residue was separated by silica gel column chromatography.Elution with petroleum ether:ethyl acetate (10:1) to collect the desired components,Evaporation under reduced pressure gave a white solid VId 6.3 g, yield 74.8%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Bromomethyl)benzo[d][1,3]dioxole, and friends who are interested can also refer to it.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Zhong Bohua; Zhang Ping; He Xinhua; Shi Weiguo; Fan Shiyong; Yao Yishan; Jia Hongxin; (20 pag.)CN103804341; (2018); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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 22385-77-9, HPLC of Formula: C14H21Br

2-(3,5-Di-t-butylphenyl)benz[f]indene (Ligand J) Benz[f]indene (10.8 g, 0.065 mole) was dissolved in 100 mL of dimethylformamide. 1-Bromo-3,5-di-t-butylbenzene (14 g, 0.052 mole) was added along with palladium acetate (0.3 g), tri-o-tolylphosphine (0.8 g), and triethyl amine (11.0 g). The solution was heated to 60 C for 3 days. The solution was cooled and washed with 1 N HCl and by saturated sodium bicarbonate. The product was found to be difficult to separate from the residual tri-o-tolylphosphine. After purifying by passing through silica with hexanes three times, and recrystallization from ethanol, followed by three recrystallizations from hexanes, it yielded 5.8 g of 2-(3,5-di-t-butylphenyl)benz[f]indene (26% yield). 1H-NMR (CDCl3, 300 MHz) delta 7.95-7.77 (m, 4H); 7.52-7.37 (m, 5H); 7.23 (s, 1H); 3.99 (s, 2H); 1.43 (s, 18H).

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, 1-Bromo-3,5-di-tert-butylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BP Corporation North America Inc.; EP1157047; (2003); B1;,
Bromide – Wikipedia,
bromide – Wiktionary