Month: May 2021

Synthetic Route of 3959-05-5, 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. 3959-05-5, name is (2-Bromophenyl)methanamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 47 Part A. (2-Bromo-benzyl)-methyl-amine A solution of 2-bromobenzylamine (9 g, 36.1 mmol) in MeOH (60 ml) was added dropwise over 30 min. to a solution of methylamine in MeOH (200 mL of a 2.0 M solution, 0.4 mol). The resulting solution was stirred at rt for 2 h and concentrated. The residue obtained was dissolved in DCM (100 mL) and successively washed with saturated aqueous sodium carbonate, dried over sodium sulphate, and concentrated. The resulting oil was distilled to afford the title compound (7 g, 95%) as a colorless oil (b.p. 110 C. at 0.1 mm Hg, LC/MS retention time=1.22 min.; M+=201.92 Column: Phenominex 4.6 mm*50 mm.

The synthetic route of (2-Bromophenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US6596747; (2003); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 117635-21-9 as follows. SDS of cas: 117635-21-9

1,4-dibromo-2,5-dihexyl benzene (8.05 mmoles, 3.255g), boronic ester 26 (17.7 mmoles, 7.545g), Na2CO3 (40.3 mmoles, 4.268g) and Aliquat 336 (0.500g) were suspended in toluene (100 mL) in a 250 mL two-necked- round-bottom-flask with stir bar and condenser. The reaction mixture degassed and Pd(PPh3)4 (0.403 mmoles, 0.465g) added followed by addition of degassed water (50 mL). Reaction heated to 90C for two days. Resulting reaction mixture diluted with ethyl acetate (150 mL), washed with ethyl acetate (3 x 100 mL). Organic layer washed with brine (2 x 100 mL), dried over magnesium sulfate, filtered and concentrated. Purification by column chromatography on silica gel using 1 :3 DCM: Hexanes to yield white powder (56%, 3.8g). 1 H NMR (500 MHz, CD2CI2) delta = 7.45 (d, J = 8.5Hz, 4H), 7.33-7.31 (m, 5H), 7.26-7.19 (m, 5H), 6.65 (s, 2H), 2.71 -2.63 (m, 9H0, 1 .54 (s, 18H), 1 .31 -1 .20 (m, 14H), 1 .15 (t, J = 7.49, 7H), 0.83 (t, J = 6.85Hz, 6H).

According to the analysis of related databases, 117635-21-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; PARK, Kyung-Ho; RADU, Nora, Sabina; JOHANSSON, Gary, A.; FENNIMORE, Adam; DELANEY, William, J.; LECLOUX, Daniel, David; WO2011/159872; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1159010-96-4, 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. 1159010-96-4 name is 3-Bromo-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, 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 mixture of 4,4,5,5-tetramethyl-2-(2-methylbiphenyl-3-yl)-1,3,2-dioxaborolane (Example 4, Step 1: 20 mg, 0.07 mmol), 3-bromo-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride (AstaTech cat SC2711: 17 mg, 0.068 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (3 mg, 0.003 mmol) and potassium carbonate (28 mg, 0.20 mmol) in 1,4-dioxane (1 mL) and water (0.5 mL) was degassed and recharged with nitrogen three times. The mixture was then heated and stirred at 110 C. overnight. The crude reaction mixture was purified by prep LCMS (pH 2, acetonitrile/water+TFA) to give the desired product as its TFA salt. LC-MS calculated for C21H21N2(M+H)+: m/z 301.2; found: 301.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Qian, Ding-Quan; Lu, Liang; Lajkiewicz, Neil; Konkol, Leah C.; Li, Zhenwu; Zhang, Fenglei; Li, Jingwei; Wang, Haisheng; Xu, Meizhong; Xiao, Kaijiong; Yao, Wenqing; (101 pag.)US2018/177784; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 121086-19-9,Some common heterocyclic compound, 121086-19-9, name is 4-Bromo-N-isopropylaniline, molecular formula is C9H12BrN, 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.

N-(4-Bromophenyl)-N-(2-propyl)-3-methyl-2-butenamide Compound 5 A solution of 3,3-dimethylacryloyl chloride (5.56 mL, 50 mmol) in 120 mL of chloroform was added to a solution of 4-bromo-N-(2-propyl)-aniline (Compound 4, 10.4 g, 48.5 mmol) in 400 mL of chloroform over 5 minutes. The reaction mixture was then refluxed overnight. After cooling to room temperature, the reaction mixture was washed with 5% HCl (1*150 mL), saturated, aqueous sodium bicarbonate (1*150 mL) and brine (1*150 mL). The organic phase was dried over anhydrous sodium sulfate and the solvent evaporated in vacuo to afford 13.8 g (96%) of the title compound as a brown solid. 1 H-NMR (300 MHz, CDCl3): d 1.05(d, J=6.8 Hz, 6H), 1.63(s, 3H), 2.08(s, 3H), 4.98(m, 1H), 5.22(br s, 1H), 6.95(d, J=8.5 Hz, 2H), 7.51(d, J=8.6 Hz, 2H).

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

Reference:
Patent; Allergan Sales, Inc.; US6048873; (2000); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 112279-60-4, name is 4-Bromo-2,5-difluoroaniline, 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 112279-60-4, category: bromides-buliding-blocks

A degassed solution of ethyl 3-(trifluoromethanesulfonyloxy)furo [3,2- c]pyridine-2-carboxylate (678 mg, 2.00 mmol), 4-bromo-2,5-difluoroaniline (670 mg, 3.22 mmol), Pd2dba3 (147 mg, 0.160 mmol), Xantphos (97.0 mg, 0.168 mmol) and finely powdered K3PO4 (793 mg, 3.74 mmol) in toluene (7.5 ml) was heated in a sealed tube at 1050C overnight. The reaction mixture was cooled to ambient temperature then diluted with ethyl acetate (15 ml) and filtered through a plug of silica gel (15 ml packed in ethyl ether). After washing the filter cake with more ethyl acetate (20 ml), the filtrate was dried over magnesium sulfate and concentrated in vacuo to give a brown oil. The residue was purified by flash chromatography (silica gel, using using 5:3:2 hexane-methylene chloride-ethyl ether) to afford the title compound as a tan solid (329 mg, 41%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,5-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; WO2008/24725; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 21865-50-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 21865-50-9 as follows.

General procedure: A mixture of starting compound (2.69 mmol), CuCl2.2H2O (10 mol %) in DMSO (5 mL) stirred at 100 C. The reaction progress was monitored by thin layer chromatography (PMA was used for stain solution). The reaction mixture was poured into ice cold water. The crude product was purified by column chromatography using ethyl acetate and petroleum ether as eluent to afford carbazoles.

According to the analysis of related databases, 21865-50-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dalvi, Bhakti A.; Lokhande, Pradeep D.; Tetrahedron Letters; vol. 59; 22; (2018); p. 2145 – 2149;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 69902-83-6, A common heterocyclic compound, 69902-83-6, name is 1-Bromo-2-methyl-3-(trifluoromethyl)benzene, molecular formula is C8H6BrF3, 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.

Step 1[00293] To a solution of l-bromo-2-methyl-3-(trifluoromethyl)benzene (CXXVII) (5.7 g, 23.86 mmol) in CC14 (50 niL) was added NBS (4.24 g, 23.86 mmol) and a catalytic amount of benzoyl peroxide. The reaction mixture was gently refluxed for 1 h. The reaction mixture was cooled to room temperature and the precipitate was removed by filtration. The solution was concentrated under reduced pressure and the crude product was dissolved in hexane and additional precipitate was removed by filtration. The filtrate was concentrated to dryness to give l-bromo-2-(bromomethyl)-3-(trifluoromethyl)benzene (CXXVIII) as an orange oil (7.51 g, 23.62 mmol). 1H NMR (DMSO-d6) delta ppm 4.73 (s, 2H), 7.4 (dd, J=8 Hz, J=8 Hz, 1H), 7.80 (d, J=8 Hz, 1H), 8.02 (d, J=8 Hz, 1H); 19 F NMR (DMSO-d6) delta ppm -57.85 (s, 3F). The crude product was used without further purification for step 2.

The synthetic route of 69902-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REMPEX PHARMACEUTICALS, INC.; GLINKA, Tomasz; HIGUCHI, Robert; HECKER, Scott; EASTMAN, Brian; RODNY, Olga; WO2012/109164; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 875664-41-8 as follows. Quality Control of 3-Bromo-4,5-difluoroaniline

Compound 99 A mixture of 3-(N-isopropylsulfamoyl)benzoic acid (2.3 g, 9.615 mmol), 3-bromo-4,5- difluoroaniline (2 g, 9.615 mmol) and DIPEA (5 mL) in CH2CI2 (30 mL) was cooled to 0C and HATU (4.39 g, 1 1.538 mmol) was added. The mixture was stirred for 2 hours at 20C. The mixture was washed with IN HC1 (30 mL) and brine (30 mL) and dried over Na2S04. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (gradient eluent: petroleum ether/ethyl acetate from 100/0 to 70/30) resulting in crude N-(3-bromo-4,5-difluorophenyl)-3-(N-isopropylsulfamoyl)- benzamide (4 g). A mixture of N-(3-bromo-4,5-difluorophenyl)-3-(N-isopropyl- sulfamoyl)benzamide (1 g, 2.308 mmol), methylboronic acid (1 g, 4.616 mmol), CS2CO3 (2.26 g, 6.924 mmol), 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (95 mg, 0.231 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.21 g, 0.231 mmol) in dioxane (15 mL) was heated by microwave irradiation for 40 minutes at 120C under N2 atmosphere. After cooling, the mixture was filtered through celite and the filtrate was evaporated to dryness. The obtained residue was purified by silca gel column chromatography (gradient eluent: petroleum ether/ethyl acetate from 100/0 to 70/30) and further purified by preparative high performance liquid chromatography over reversed phase C-18 (eluent: CH3CN in H20 (0.1% TFA) from 38% to 68%, v/v). The pure fractions were collected and half of the volatiles were removed in vacuo. The mixture was adjusted to pH=7 with Amberlite IRA-900 (OH) anionic exchange resin and the resin was filtered off. The organic solvent was concentrated in vacuo and the aqueous layer was lyophilized to dryness. The obtained product was further purified by silica gel chromatography (gradient eluent: petroleum ether/ethyl acetate from 100/0 to 70/30) resulting in compound 99 (190 mg). Method A; Rt: 6.09 min. m/z : 369.2 (M+H)+ Exact mass: 368.1, 1H NMR (400 MHz, CHLOROFORM- ) delta ppm 8.35 (1 H, t, J=1.5 Hz), 8.09 – 8.17 (2 H, m), 8.04 (1 H, dt, J=8.0, 1.5 Hz), 7.66 (1 H, t, J=8.0 Hz), 7.54 (1 H, ddd, J=11.5, 6.5, 3.0 Hz), 7.14 – 7.22 (1 H, m), 4.72 (1 H, d, J=8.0 Hz), 3.43-3.60 (1 H, m), 2.32 (3 H, d, J=2.0 Hz), 1.10 (6 H, d, J=6.5 Hz).

According to the analysis of related databases, 875664-41-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN R&D IRELAND; LAST, Stefaan Julien; RABOISSON, Pierre Jean-Marie Bernard; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim Gaston; WO2014/33170; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 41825-73-4, 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. 41825-73-4 name is 2-Bromo-4,6-dimethylaniline, 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.

General procedure: 2-iodoaniline (0.5 mmol) or 2-bromoaniline (0.5 mmol), complex 1 (0.05mmol), K2CO3 (1 mmol), (n-Bu)4NBr (0.1 mmol) and water (10 mL) were added to a sealed tube. The reaction mixture was stirred at 120oC for 30 h, then cooled to room temperature and then extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and the solvent was then removed under reduced pressure. The product was finally obtained by column chromatography on silica gel.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4,6-dimethylaniline, and friends who are interested can also refer to it.

Reference:
Short Survey; Yu, Lintao; Zhou, Xiangge; Wu, Di; Xiang, Haifeng; Journal of Organometallic Chemistry; vol. 705; (2012); p. 75 – 78;,
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. 627526-90-3, name is 1-Bromo-3-(difluoromethyl)-5-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H4BrF3

(B) To a solution of 1-bromo-3-(difluoromethyl)-5-fluorobenzene (8.6 g, 38.56 mmol, I eq) and DIPEA(13.44 ml, 77.12 mmol, 2 eq) in 1,4-dioxane (150 ml) was added PMB-SH (5.89 ml, 42.42 mmol, 1.1 eq).The mixture was degassed for 10 mm, and Xantphos (1.56 g, 2.69 mmol, 0.07 eq), followed by Pd2(dba)3 (1.0 g, 1.15 mmol, 0.03 eq) were added. The mixture was again degassed for 10 mm. The resulting RM was heated to 90 C and stirred for 2 h under Ar. The RM was filtered through celite and the filtrate concentrated to yield the crude product, which upon flash chromatography afforded 1 -bromo-3-(difluoro-methyl)-5-fluorobenzene (10 g, 87%).

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 627526-90-3.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary