Category: 4044-58-0

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. 4044-58-0, name is 1-Bromo-8-iodonaphthalene, A new synthetic method of this compound is introduced below., SDS of cas: 4044-58-0

Ethylmagnesium bromide (11.6 mL, 11.0 mmol; 0.95 M solution in THF) was added slowly over8 min to a solution of phenylacetylene (1.21 mL, 11.0 mmol) in THF (10 mL) at room temperature andthe mixture was stirred for 40 min at room temperature. The resulting solution was then added slowlyover 6 min with additional THF (3 mL) to ZnCl2 (1.64 g, 12.0 mmol) at 0 C, and the mixture wasstirred for 30 min at 0 C. Pd(PPh3)4 (300 mg, 0.260 mmol) and 1-bromo-8-iodonaphthalene (3.33 g,10.0 mmol) were successively added to it with THF (2 mL) and the mixture was stirred for 17 h atroom temperature. The reaction was quenched with 1 M HClaq and diluted with H2O. After extractionwith Et2O, the organic layer was washed with saturated NaClaq, dried over MgSO4, filtered, andconcentrated under vacuum. The residue was chromatographed on silica gel with hexane to afford 1-bromo-8-(phenylethynyl)naphthalene (CAS 4404-55-7) as a yellow oil (2.20 g, 7.16 mmol; 72% yield).

The synthetic route of 4044-58-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maesato, Takumi; Shintani, Ryo; Chemistry Letters; vol. 49; 4; (2020); p. 344 – 346;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 4044-58-0, These common heterocyclic compound, 4044-58-0, name is 1-Bromo-8-iodonaphthalene, 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 Cul (1.57 g, 8.26 mmol, 1.1 eq) and KF (479 mg, 8.26 mmol, 193 pL, 1.1 eq) was thoroughly mixed and heated to 150 C under vacuum by using oil pump with heat gun with gentle shaking until an homogemeous greenish color was obtained. To the mixture was added DMSO (50 mL), trimethyl(trifluoromethyl)silane (3.20 g, 22.5 mmol, 3.0 eq) and l-bromo-8-iodo-naphthalene (2.5 g, 7.51 mmol, 1.0 eq) was added and the slurry was heated to 25 C for 16 h. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (3 c 30 mL). The combined organic layers were washed with brine (20 mL), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-HPLC (column: Phenomenex Synergi C18 150*25* lOpm; mobile phase: [water (0.225% FA) – ACN]; B%: 66%- 86%, lOmin). l-bromo-8- (trifluoromethyl)naphthalene (900 mg, 3.14 mmol, 42% yield, 96% purity) was obtained as a white solid. (0758) [0436] *H NMR (400MHz, chloroform-d) d = 8.12 (d, J= 7.6 Hz, 1H), 8.10 – 8.02 (m, 2H), 7.90 (dd, J = 1.2, 8.0 Hz, 1H), 7.54 (t, J= 7.6 Hz, 1H), 7.37 (t, .7= 7.6 Hz, 1H).

Statistics shows that 1-Bromo-8-iodonaphthalene is playing an increasingly important role. we look forward to future research findings about 4044-58-0.

Reference:
Patent; MIRATI THERAPEUTICS, INC.; ARRAY BIOPHARMA, INC.; MARX, Matthew, Arnold; BLAKE, James, F.; FELL, Jay, Bradford; FISCHER, John, P.; MEJIA, Macedonio, J.; (164 pag.)WO2020/47192; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com