Category: 5279-32-3

Application of 5279-32-3, These common heterocyclic compound, 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, 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 29: Preparation of N-(4-(6-bromobenzo[d] [l,3]dioxol-5-yl)phenyl)-2,6- difluorobenzamide (81):; Preparation of 4-(6-bromobenzo[d] [l,3]dioxol-5-yl)aniline (80):; Palladium tetrakis-triphenylphosphine (67 mg, 58 muiotaetaomicron) was added to a degassed solution of bromide 78 (323 mg, 1.15 mmol) and boronic acid 79 (200 mg, 1.15 mmol) in dioxane : acetonitrile : water (9:9:2, 7.6 mL) and potassium carbonate (679 mg, 3.2 mmol). The resulting mixture was heated under argon at 90 C with stirring for 1 h. The mixture was then cooled, diluted with dichloromethane (9 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-2.5% methanol in dichloromethane) provided 80 (150 mg, 45%) as a solid: LRESIMS m/z 292.1 [M+H]+, calcd. for Ci3H11Br1N102 292.0.

Statistics shows that 5,6-Dibromobenzo[d][1,3]dioxole is playing an increasingly important role. we look forward to future research findings about 5279-32-3.

Reference:
Patent; CALCIMEDICA, INC.; WHITTEN, Jeffrey P.; PEI, Yazhong; CAO, Jianguo; WANG, Zhijun; ROGERS, Evan; DYCK, Brian; GREY, Jonathan; WO2011/139765; (2011); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 5279-32-3, These common heterocyclic compound, 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, 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, Method 25: ll-(2-Chlorophenyl)-4,6,10-trioxa-12- azatricyclo[7.3.0.03’7]dodeca-l,(9),2,7,ll-tetraene[0251] A mixture of 5,6-dibromo-2H-l,3-benzodioxole (500 mg, 1.79 mmol), 2- chlorobenzamide (300 mg, 1.93 mmol), potassium carbonate (1.0 g, 7.24 mmol), N,N-dimethylethane-l,2-diamine (50 mu,, 0.57 mmol) and copper(I) iodide (35 mg, 0.18 mmol) in toluene (30 mL) and 1,4-doxane (30 mL) was stirred under reflux for 24 hours. After cooling to room temperature the mixture was diluted with ethyl acetate (50 mL), filtered and concentrated. The residue was taken up in ethyl acetate (150 mL), washed with water (50 mL) and brine (50 mL), dried over magnesium sulphate, filtered and absorbed onto a small amount of silica. Purification by FCC (silica, 0-20% ethyl acetate in heptane) and recry stallis ation from 5% ethyl acetate in heptane (10 mL) gave the title compound 120 mg (25% yield) as a colourless, crystalline solid. 5H MR (500 MHz, DMSO) 8.09 (dd, J = 7.7, 1.8 Hz, 1H), 7.69 (dd, J = 7.9, 1.2 Hz, 1H), 7.59 (td, J = 7.7, 1.8 Hz, 1H), 7.55 (td, J = 7.5, 1.3 Hz, 1H), 7.51 (s, 1H), 7.41 (s, 1H), 6.14 (s, 2H). Tr(MET-uHPLC-AB-lOl) = 3.66 min, (ES+) (M+H)+274.

The synthetic route of 5279-32-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; BROWN, Christopher, John; PRIME, Michael, Edward; WEDDELL, Derek, Alexander; WALTER, Daryl, Simon; GILES, Paul, Richard; WIGGINTON, Ian, James; TAYLOR, Malcolm, George; GALAN, Sebastien, Rene, Gabriel; JOHNSON, Peter, David; KRUeLLE, Thomas, Martin; MORAO, Inaki; CLARK-FREW, Daniel; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; (120 pag.)WO2016/33460; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, A new synthetic method of this compound is introduced below., Safety of 5,6-Dibromobenzo[d][1,3]dioxole

A stirred solution of 5,6-dibromobenzo[d][1,3]dioxole S6 (400 mg, 1.43 mmol) in toluene (15 mL) was cooled at -78 C, and freshly distilled furan (0.51 mL, 7.15 mmol) was added to the solution. n-BuLi (1.38 M in THF, 1.14 mL, 1.57 mmol) was added dropwise to the resulting solution over 5 minutes at -78 C. The reaction mixture was stirred for 10 additional minutes before it was warmed up to -40 C. Stirringwas continued for another 2 hours before water (20 mL) was added to quench the reaction. The organic layerwas separated and the aqueous layer was extracted with Et2O (4 x 10 mL). The combined organic extracts were washed with brine (20 mL), dried over Na2SO4, and concentrated in vacuo. Purification by column chromatography on silica gel, eluting with PET/Et2O (80:20), afforded 5,8-dihydro-5,8-epoxynaphtho[2,3-d][1,3]dioxole S7 (241 mg, 1.28 mmol, 90 %) as a white crystalline solid.

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:
Article; Antien, Kevin; Viault, Guillaume; Pouysegu, Laurent; Peixoto, Philippe A.; Quideau, Stephane; Tetrahedron; vol. 73; 26; (2017); p. 3684 – 3690;,
Bromide – Wikipedia,
bromide – Wiktionary