4,4'-DIFLUORODIPHENYLACETYLENE synthesis
- Product Name:4,4'-DIFLUORODIPHENYLACETYLENE
- CAS Number:5216-31-9
- Molecular formula:C14H8F2
- Molecular Weight:214.21
Yield: 60%
Reaction Conditions:
with bis-triphenylphosphine-palladium(II) chloride;copper(l) iodide;diisopropylamine at 100; for 95 h;Inert atmosphere;
Steps:
5.3 Bis(4-fluorophenyl)acetylene (3)
Diethynyldiphenylsilane (100 mg, 0.44 mmol) and1-bromo-4-fluorobenzene (0.24 mL, 2.2 mmol) were dissolvedin diisopropylamine (15 mL). The solution wasdegassed two times and CuI (17 mg, 0.09 mmol) andPdCl2(PPh3)2 (62 mg, 0.09 mmol) were added. The yellowsolution was heated to 100°C for 95 h, then quenched withsat. aqueous NH4Cl solution (15 mL) and extracted withDCM (40 mL). The organic phases were dried over MgSO4,and all volatile compounds were removed in vacuum.Sublimation (50°C, 6 × 10-2 mbar) gave bis(4-fluorophenyl)acetylene as a colorless solid. Yield: 110 mg (0.53 mmol,60%). - 1H NMR (500 MHz, CDCl3): δ = 7.50 (m, 4H,o-PhH), 7.05 (m, 4H, m-PhH) ppm. - 13C{1H} NMR (125 MHz,CDCl3): δ = 162.7 (d, J = 249.7 Hz), 133.6 (d, J = 8.4 Hz), 119.3(d, J = 3.5 Hz), 115.8 (d, J = 22.1 Hz), 88.1 ppm. - 19F NMR(470 MHz, CDCl3): δ = -110.8 (tt, J = 8.6, 5.4 Hz) ppm.
References:
Horstmann, Jan;Reger, Stefanie;Neumann, Beate;Stammler, Hans-Georg;Mitzel, Norbert W. [Zeitschrift fur Naturforschung, B: Chemical Sciences,2017,vol. 72,# 7,p. 489 - 495]
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