4,4'-BIS(4-TRIFLUOROVINYLOXY)BIPHENYL synthesis

Yield:134130-19-1 60%

Reaction Conditions:

with zinc in acetonitrile;Reflux;

Steps:

2.3.5. Synthesis of 4,40-bis(trifluorovinyloxy)biphenyl (4,4'-TFVE)

To a 100 mL round-bottom flask equipped with a condenser anda magnetic stirrer were added 8.24 g (15.15 mmol) of 4,4'-bis(2-bromo-tetrafluoroethoxy) biphenyl, 3 g (45 mmol) of actived zincand 50 mL of acetonitrile. The mixture was refluxed and the reactionwas monitored by 19F NMR. After completion of the reaction,the excess of zinc and salts formed were filtered over celite andwashed with diethyl ether. 200 mL of water were added to thefiltrate which was extracted several times with diethyl ether. Theorganic phase was dried over sodium sulfate, filtered and the solventwas removed. The crude product was purified by chromatographyon silica gel using petroleum ether as eluent to give 3.15 gof a white solid (60% yield). 19F NMR (DMSO-d6, 188 MHz): d 118.48 (dd, F1, JF1-F2 97.8 Hz,JF1-F3 56.4 Hz), 126.36 (dd, F2, JF2-F1 97.8 Hz, JF2-F3 109.0 Hz), 134.20 (dd, F3, JF3-F2 109.0 Hz, JF3-F1 56.4 Hz).1H NMR (DMSO-d6, 200 MHz): d 7.72 (d, 2H2, JH-H 8.0 Hz), 7.36 (d,2H3, JH-H 8.0 Hz). 13C NMR (DMSO-d6, 50 MHz): d 153.74 (C4),136.11 (C1), 128.61 (C2), 116.12 (C3).

References:

Marestin, Catherine;Thiry, Xavier;Rojo, Sergio;Chauveau, Edouard;Mercier, Regis [Polymer,2017,vol. 108,p. 179 - 192]