ChemicalBook CAS DataBase List 4,4'-Divinylbiphenyl

4,4'-Divinylbiphenyl synthesis

11synthesis methods

Product Name:4,4'-Divinylbiphenyl
CAS Number:4433-13-0
Molecular formula:C16H14
Molecular Weight:206.28

The preparation of 4,4'-Divinylbiphenyl is as follows: Reaction flask (10 mL) equipped with stirring bar was charged with 4-vinylphenylboronic acid (135mg, 0.91 mmol), ethanol (96%) (2 mL), [{Pd(μ-OH)Cl(IPr)}2] (510-4 g, 4.55 × 10-7 mol). Reactionmixture was stirred at 22 C for 6 h. After completion of the reaction solvent was evaporated, theresidue was dissolved in hexane (5 mL) and extracted with water (2 × 2 mL). The organic layer wasdried over magnesium sulphate, and hexane was evaporated under reduced pressure. 176 mg of 4,4'-divinylbiphenyl was obtained as a white solid. Yield = 93%.

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4433-13-0
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Yield: 93%

Reaction Conditions:

with C₅₄H₇₄Cl₂N₄O₂Pd₂ in ethanol at 22; for 6 h;

Steps:

4,4'-divinylbiphenyl S6 (3i)
Reaction flask (10 mL) equipped with stirring bar was charged with 4-vinylphenylboronic acid (135mg, 0.91 mmol), ethanol (96%) (2 mL), [{Pd(μ-OH)Cl(IPr)}2] (510-4 g, 4.55 × 10-7 mol). Reactionmixture was stirred at 22 C for 6 h. After completion of the reaction solvent was evaporated, theresidue was dissolved in hexane (5 mL) and extracted with water (2 × 2 mL). The organic layer wasdried over magnesium sulphate, and hexane was evaporated under reduced pressure. 176 mg of 4,4'-divinylbiphenyl was obtained as a white solid. Yield = 93%. 1H NMR (403 MHz, CDCl3, ppm) δ: 7.58(d, J = 8.4 Hz, 4H), 7.49 (d, J = 8.3 Hz, 4H), 6.76 (dd, J = 17.6, 10.9 Hz, 2H), 5.80 (d, J = 18.4 Hz,2H), 5.28 (d, J = 10.9 Hz, 2H); 13C NMR (101 MHz, CDCl3, ppm) δ: 140.0, 136.6, 136.3, 127.0,126.7, 126.6, 113.9. MS (EI) m/z (%) = 206 (M+, 100), 179 (9), 153 (10), 103 (8), 27 (10).

References:

Ostrowska, Sylwia;Rogalski, Szymon;Lorkowski, Jan;Walkowiak, Jedrzej;Pietraszuk, Cezary [Synlett,2018,vol. 29,# 13,p. 1735 - 1740] Location in patent:supporting information

2039-82-9 Synthesis