Reference of 766-46-1,Some common heterocyclic compound, 766-46-1, name is 2′-Bromophenylacetylene, molecular formula is C8H5Br, 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 10 mL screw cap vial, copper(I) 3-methylsalicylate (5.4 mg, 0.025 mmol), a cold (-20 C.) solution of azidotrifluoromethane in THF (?1.5 mmol, 3-4 mL) and a solution of 2-bromophenylacetylene (1.0 mmol) in THF (0.5 mL) were added. The vial was closed and the content stirred at rt for 18 h. THF was removed under reduced pressure, Et2O (20 mL) was added and the organic phase was washed with aqueous NaHCO3 (5%, 2*10 mL), water (10 mL), aqueous LiCl (1 mol¡¤l-1, 10 mL) and brine (10 mL), dried (MgSO4), filtered and solvent was removed under reduced pressure. Purification by column chromatography (silicagel) gave the product as a yellow oil. Yield 84%; Rf (cyklohexane:EtOAc, 97:3)=0.27; IR (CHCl3, film)=1420, 1206, 1191, 760 cm; 1H NMR (400 MHz, CDCl3) delta=8.63 (s, 1H), 8.16-8.14 (ddd, J=7.8, 1.7, 0.4 Hz, 1H), 7.71-7.69 (ddd, J=8.1, 1.3, 0.4 Hz, 1H), 7.49-7.45 (ddd, J=7.9, 7.4, 1.3 Hz, 1H), 7.31-7.27 (ddd, J=8.1, 7.4, 1.8 Hz, 1H); 13C NMR (101 MHz, CDCl3) delta=146.1, 133.8, 131.0, 130.5, 129.4, 128.0, 121.4, 120.6, 117.7 (q, 1JC-F=268.4 Hz); 19F NMR (376 MHz, CDCl3) delta=-59.2 (s); HRMS (ESI) m/z calculated for C9H6N3F3Br [M+H]+: 291.9692, found 291.9692.
The synthetic route of 766-46-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Ustav organicke chemie a biochemie AV CR, v.v.i.; CF Plus Chemicals s.r.o.; BEIER, Petr; MATOUSEK, Vaclav; BLASTIK, Zsofia E.; VOLTROVA, Svatava; (12 pag.)US2019/161452; (2019); A1;,
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