Bromides-buliding-blocks

Some common heterocyclic compound, 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, molecular formula is C6H3BrF2, 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. 38573-88-5

EXAMPLE 200 Step-1: n-Butyl lithium (0.895 g, 0.0140 mol, 1.6 M in hexane) was added dropwise to a stirred solution of 2, 3-difluorobromobenzene (3.0 g, 0.0155 mol) in THF (40 ml) over a period of 20 min at -78 0C, and reaction was continued stirring for 2 h at the same temperature. Then, 4,6-dichloropyrimidine (2.316 g, 0.0155 mol) in THF (20 ml) was added drop wise to the generated 2,3-difluorophenyl lithium mixture over a period of 15 min at -78 ¡ãC, and reaction was continued stirring for 30 min. Then, the reaction mixture was slowly warmed to 0 ¡ãC and was quenched with water (30 ml), and then DDQ (3.53 g, 0.0155 mol) in THF (30 ml) was added portionwise with stirred for 10 min. The resultant reaction mixture was extracted with CH2Cl2 (3×50 ml), washed with brine (50 ml), dried (Na2SO4), and concentrated. The concentrated product was purified through silica column chromatography using pet. ether to afford step-1 product (1.1g, 27.1 percent) as an off white solid. Rf: 0.3 (100percent PE). 1H NMR (400 MHz, CD3OD): delta 8.82 (s, IH), 7.91-7.78 (m, IH), 7.48-7.45 (m, IH), 7.32-7.26 (m, IH). m/e (M+l): 260.8

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 38573-88-5, its application will become more common.

Reference:
Patent; MIIKANA THERAPEUTICS, INC.; WO2008/154026; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 69321-60-4, name is 2,6-Dibromotoluene, 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 69321-60-4. 69321-60-4

6-Dimethylamino-3,4-dihydro-2H-isoquinolin-l-one (150mg, 0.789mmol), cuprous iodide (30mg, O.lbetammol) and potassium carbonate (109mg, 0.789mmol) were deposited in a sealed vessel. 3 mL DMSO and 2,6-dibromotoluene (395mg, 1.58mmol) were added. Argon was bubbled through the mixture for 2 minutes and the lid was tightly closed. This was heated at 1500C for 24 hours. Cuprous iodide (30mg, O.lbetammol) was added and the mixture was heated at 1500C for an additional 24 hours. This was diluted with dichoromethane and filtered through a pad of celite. The filtrate was partitioned between DCM and 5% aq. ammonium hydroxide. The DCM layer was washed with brine. The combined aqueous layers were washed with DCM. The combined DCM layers were dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (gradient elution 25 to 50% ethyl acetate/hexanes) to yield 2-(3-Bromo-2-methyl-phenyl)-6-dimethylamino-3,4-dihydro-2H-isoquinolin-l-one (181mg, 0.504mmol). MS (ESI) 361.1 (M+H)+.

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 2,6-Dibromotoluene.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2009/98144; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

A common compound: 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 73918-56-6

To a stirring solution of 4-dimethylaminopyridine (0.19 g, 1.5 mmol) and di-tert-butyl dicarbonate (2.6 g, 12 mmol) in dichloromethane (40 mL) was added 4-bromophenethylamine (1.6 mL, 10 mmol) and stirred at room temperature for 48 hours. The reaction mixture directly adsorbed onto silica gel and purified by flash column chromatography using 0-40% ethyl acetate/hexanes as eluent to afford the title compound as a white solid (0.68 g, 22%): mp 58-59 C.; 1H NMR (400 MHz, CDCl3) delta 7.42 (d, J=8.3 Hz, 2H), 7.07 (d, J=8.3 Hz, 2H), 4.51 (s, 1H), 3.43-3.27 (m, 2H), 2.75 (t, J=7.0 Hz, 2H), 1.43 (s, 9H); 13C NMR (101 MHz, CDCl3) delta 155.79, 137.97, 131.62, 130.55, 120.25, 77.21, 41.58, 35.65, 28.39; EIMS m/z 301 ([M]+).

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, 73918-56-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DOW AGROSCIENCES LLC; Fischer, Lindsey G.; Baum, Erich W.; Crouse, Gary D.; DeAmicis, Carl; Lorsbach, Beth; Petkus, Jeff; Sparks, Thomas C.; Whiteker, Gregory T.; US2014/274688; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary