1,2-di([1,1'-biphenyl]-4-yl)ethyne synthesis
- Product Name:1,2-di([1,1'-biphenyl]-4-yl)ethyne
- CAS Number:21326-80-7
- Molecular formula:C26H18
- Molecular Weight:330.42
Yield:21326-80-7 60%
Reaction Conditions:
with tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane at 100; for 2 h;Inert atmosphere;Stille coupling;
Steps:
Bis(4-biphenyl)acetylene (9).
Tetrakis(triphenylphosphino) palladium(0) (0.28 g, 1.3 mol%), 4-bromobiphenyl (9.05 g, 38.8 mmol, 2.02 eq.), 1 (11.5 g, 19.2 mmol) and p-dioxane (75 mL) were combined in a Schlenk flask and heated to 100 °C for 2 h. Plate-like crystals formed upon cooling. The crystals were filtered and were rinsed with hexanes. The crystals were recrystallized from hot toluene, resulting in large colorless plates of 9 (3.89 g, 60%). m. p.: 245-247 °C. 1H NMR (CDCl3; 300.17 MHz): d 7.64-7.61 (m, 12 H), 7.49-7.44 (m, 4 H), 7.39-7.34 (m, 2 H). 13C NMR (CDCl3; 75.485 MHz): d 141.0, 140.4, 132.1 (C-H), 128.9 (C-H), 128.6 (C-H), 127.7 (C-H), 127.1 (C-H), 122.3, 90.0 (acetylene). UV/Vis (toluene): no lmax >295 nm (tails to 365 nm). HR-MS (EI): for C26H18: calc’d: 330.1409; found: 330.1404.
References:
Brown, Amy E.;Eichler, Barrett E. [Tetrahedron Letters,2011,vol. 52,# 16,p. 1960 - 1963] Location in patent:supporting information; experimental part
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