Tag: M.W=100-200

These common heterocyclic compound, 583-75-5, name is 4-Bromo-2-methylaniline, 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. Formula: C7H8BrN

EXAMPLE 192 1,2-Dihydro-6-(3-nitrophenyl)-2,2,4,8-tetramethylquinoline (Compound 292, structure 86 of Scheme XXII, where R1 =R3-5 =H, R2 =nitro) 4-Bromo-2-methylaniline (5.58 g, 30 mmol) was treated with iodine (0.2 g, 0.9 mmol) and acetone (150 mL) in a sealed tube at 80 C. for 24 h to provide 6-bromo-1,2-dihydro-8-methylquinoline (Compound 85 of Scheme XXII) in 9% yield as a yellow oil (0.70 g). Most of the aniline (>80%) was recovered.

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

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688808; (1997); A;,
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. 2924-09-6, name is 5-Bromo-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Bromo-2-fluoroaniline

Under an argon atmosphere, 5-bromo-2-fluoro stirring by addition of water (120mL) to the aniline (45.6g, 240mmol) and, after the addition of concentrated hydrochloric acid (120mL), cooled to -20 , and sodium nitrite ( 19.9g, was added dropwise an aqueous solution of 288mmol) and water (80mL). After stirring 20 minutes at -20 ,Adding an aqueous solution of potassium iodide (59.8g, 360mmol) and water (60mL), andIt was stirred for 30 minutes. After extraction with hexane, the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, sodium sulfite solution and dried over sodium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by a silica gel column chromatographyPurified5-Bromo-2-fluoro-iodobenzene (54.6g, 181mmol)(Yield: 76%).

According to the analysis of related databases, 2924-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Idemitsu Kosan Corporation; Hayama, Tomoharu; Kawamura, Masahiro; Mizuki, Yumiko; Ito, Hirokazu; Haketa, Tasuku; (50 pag.)KR2016/18458; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 4333-56-6,Some common heterocyclic compound, 4333-56-6, name is Bromocyclopropane, molecular formula is C3H5Br, 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 stirred solution of cyclopropyl bromide (4.0 mL, 50 mmol) in 120 mL of ether at ?78 C. was added dropwise a 1.7M solution of t-butyllithium in pentane (44.5 mL, 75.7 mmol). After 10 min, cooling bath was removed, stirring was continued for 1.5 h. The mixture was cooled again in a ?78 C. bath, and 3-furaldehyde (3.5 mL, 41.9 mmol) was added. Reaction was continued for 1 h, and quenched with a saturated NH4Cl aqueous solution. The aqueous mixture was extracted with CH2Cl2 (100 mL?3). The organic extracts were washed with brine, dried by Na2SO4, filtered, and concentrated in vacuo to give 5.3 g (91%) of the alcohol product as a yellow oil.

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

Reference:
Patent; Schering Corporation; US2004/106794; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 766-46-1, 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. 766-46-1, name is 2′-Bromophenylacetylene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of sulfonyl azides 1 (0.6 mmol), o-bromo-phenylacetylenes 2 (0.5 mmol), aromatic amines 3 (0.55 mmol), and CuI (0.05 mmol) in DMSO (2 mL) in Schlenk tube was added TEA (0.5 mmol) slowly via a syringe. The reaction solution was stirred at room temperature under N2 for 2 h. The solution was then added to CuI (0.05 mmol), K2CO3 (1 mmol), and l-proline (0.2 mmol), and the mixture was stirred at 60 C under N2 for 4 h. The reaction mixture was partitioned between ethyl acetate and saturated aq NH4Cl, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel with petroleum ether and ethyl acetate (6:1 to 9:1).

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′-Bromophenylacetylene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jin, Hongwei; Zhou, Bingwei; Wu, Zhi; Shen, Yang; Wang, Yanguang; Tetrahedron; vol. 67; 6; (2011); p. 1178 – 1182;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 766-46-1, name is 2′-Bromophenylacetylene, 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 766-46-1, Recommanded Product: 766-46-1

General procedure: A mixture of 2-ethynylbenzaldehyde (12a) (1.00 g, 7.68 mmol), 1-bromo-2-iodo-benzene (13a) (1.18 mL, 9.22 mmol), CuI (146 mg, 0.77 mmol), PdCl2(PPh3)2 (107 mg, 0.15 mmol), and Et3N (15 mL) in THF (15 mL) was stirred at 80 C for 2 h under argon, and filtrated through a pad of Celite. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography over silica gel with hexane-EtOAc (15:1).

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

Reference:
Article; Tokimizu, Yusuke; Ohta, Yusuke; Chiba, Hiroaki; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki; Tetrahedron; vol. 67; 29; (2011); p. 5168 – 5175;,
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 630-17-1 as follows. Computed Properties of C5H11Br

To a suspension of magnesium turnings (15.42 g, 634 mmol) and iodine (3 tablets) in anhydrous diethyl ether (10 ml) was added neopentyl bromide (77 ml, 601 mmol) dropwise over 2 hr under nitrogen at room temperature ) In dry ether (290 ml) was added dropwise to maintain a slight reflux, and then the mixture was refluxed for 1 hr and then allowed to cool to room temperature. The resulting Grignard reagent was added dropwise to a solution of 3-bromobicyclo [4.2.0] octa-1,3,5-trien-7-one (100 g, 510 mmol) in dry ether (1000 ml) In order to maintain the internal temperature ~ 0 c. The reaction mixture was allowed to warm to room temperature overnight, then it was cooled to 0 C, quenched with dilute hydrochloric acid (340 ml, 2 M aq) and allowed to warm to room temperature. The organic phase was washed with water (3 x 120 ml), dried over MgSO4 and the solvent was removed under reduced pressure to yield an orange oil (134 g). The oil was purified by silica gel plugs (eluted with hexane: ethyl acetate (95: 5%) to give the title product as a mixture of two isomers in an orange oil (111.1 g, 0.40 mol, 78% , 91.8% purity by 4 NMR).

According to the analysis of related databases, 630-17-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CAMBRIDGE DISPLAY TECHNOLOGY LIMITED; SUMITOMO CHEMICAL CO., LTD.; KAMTEKAR, KIRAN; BOURCET, FLORENCE; ZUBERI, TANIA; KUGLER, THOMAS; (75 pag.)TW2016/5767; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 3017-70-7, A common heterocyclic compound, 3017-70-7, name is 2-Bromo-3-methyl-2-butene, molecular formula is C5H9Br, 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.

Example 188 N-(3-Methyl-2-butenyl)-2-pyrrolidinone from a Vinyl Bromide A 15 mL screw top test tube fitted with a PTFE septum cap was charged with CuI (10.0 mg, 0.05 mmol, 5 mol %) and K2CO3 (276 mg, 2.00 mmol). 2-Pyrrolidinone (76 muL, 1.00 mmol), 2-bromo-3-methyl-2-butene (116 muL, 1.00 mmol), N,N’-dimethyl ethylenediamine (11 muL, 0.10 mmol, 10 mol %), and 1,4-dioxane (1 mL) were added, via syringe, while purging with nitrogen. The septum cap was replaced with a solid, Teflon-lined cap and the reaction was stirred magnetically at 100 C. for 38 h. The resulting heterogeneous solution was allowed to cool before dilution with 5 mL ethyl acetate. The reaction mixture was filtered and the solution obtained was concentrated to a yellow oil. The crude material was purified by silica gel chromatography using methylene chloride:ethyl acetate (80:20); the product was isolated, as a yellow oil, in 69% yield (105.3 mg). 1H NMR (300 MHz, CDCl3): ?1.60 (d, J=1.4 Hz, 3H), 1.74 (s, 3H), 1.79 (dd, J=1.3, 1.1 Hz, 3H), 2.14 (m, 2H), 2.42 (t, J=8.1 Hz, 2H), 3.44 (t, J=6.8 Hz, 2H). 13C NMR (75.5 MHz, CDCl3): 14.9, 18.5, 19.4, 19.5, 30.9, 47.5, 124.9, 129.0, 173.2.

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; Buchwald, Stephen L.; Klapars, Artis; Antilla, Jon C.; Job, Gabriel E.; Wolter, Martina; Kwong, Fuk Y.; Nordmann, Gero; Hennessy, Edward J.; US2003/65187; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 39478-78-9, name is 5-Bromo-2-methylaniline, 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. COA of Formula: C7H8BrN

Step A: N-(5-bromo-2-methylphenyl)-3,3-dimethylbutanamide 3,3-Dimethylbutanoyl chloride (1.0 g, 5.4 mmol) was added to a solution of 5-bromo-2-methylaniline (0.796 g, 5.9 mmol) in acetonitrile (10 mL). The reaction mixture was stirred at room temperature overnight. Water was added to the mixture and the precipitate formed collected to yield the title compound (0.9 g, 60%) as a white powder.

The synthetic route of 5-Bromo-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Valeant Pharmaceuticals North America; US2008/45534; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

348-57-2, name is 1-Bromo-2,4-difluorobenzene, 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. category: bromides-buliding-blocks

1-Bromo-2,4-difluoro-5-nitrobenzene To a stirred solution of 1-bromo-2,4-difluorobenzene (0.512 g, 2.65 mmol, Aldrich, used as received) in conc. H2 SO4 (5.0 mL) at 0° C., KNO3 (0.275 g, 2.72 mmol) was added in one portion. The resulting solution was allowed to warm to 28° C. and was stirred at that temperature overnight. It was then poured into ice (50 g) and extracted with ethylacetate (50 mL). The extract was dried over Na2 SO4, and evaporated to afford 0.576 g (91percent) pure title compound as light red oil; 1 H NMR (CDCl3); delta7.141 (dd, 1H, J1 10.2 Hz, J2 =7.8 Hz), 8.375 (t, 1H, J=7.5 Hz).

The synthetic route of 348-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The State of Oregon, acting by and through The Oregon State Board of Higher Education, acting for and on behalf of The Oregon Health Sciences University; The University of Oregon; The Regents of the University of California; US5514680; (1996); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 10485-09-3,Some common heterocyclic compound, 10485-09-3, name is 2-Bromoindene, 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.

Preparation of 2-Ethylindene 2-Bromoindene (8.1235 g, 0.04211 moles) and Ni(dppp)Cl2 (0.1536 g, 2.83*10-4 moles) were stirred in diethylether (100 mL) at -78 C. under a nitrogen atmosphere as ethylMgBr (0.045 moles, 15.00 mL of 3.0 M solution in diethylether) was added. The dry-ice bath was then removed and the reaction mixture allowed to warm to room temperature. The reaction mixture started off as a heterogeneous brick-red color and then turned to a homogeneous yellow/gold solution and then back to the heterogeneous brick-red mixture during the course of the warm-up. Gas chromatographic analysis after 2 hours of stirring at room temperature showed that the reaction was substantially quantitative. After the reaction period the mixture was poured onto ice and then extracted with 1 M HCL (1*100 mL) and 1 M NaHCO3 (1*100 mL) and then dried with MgSO4 and filtered. The desired product was isolated as a light yellow oil (5.65 g, 93.1 percent). 1 H NMR (300 MHz, CDCl3, TMS): delta1.31 (t, 3 JHH =7.4 Hz, 3H), 2.59 (q, 3 JHH =7.4 Hz, 2H), 3.39 (s, 2H), 6.59 (s, 1H), 7.16-7.38 (m, 3H), 7.46 (d, 3 JHH =7.4 Hz, 1H). 13 C NMR (75 MHz, CDCl3): delta13.65, 24.63, 41.23, 119.96, 123.47, 123.60, 125.25, 126.29, 143.12, 145.76, 152.47. GC-MS: Calculated for C11 H12 144.22, found 144.10.

The synthetic route of 10485-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dow Chemical Company; US6015868; (2000); A;,
Bromide – Wikipedia,
bromide – Wiktionary