ChemicalBook CAS DataBase List 1,4-di(furan-2-yl)benzene

1,4-di(furan-2-yl)benzene synthesis

6synthesis methods

Product Name:1,4-di(furan-2-yl)benzene
CAS Number:34121-64-7
Molecular formula:C14H10O2
Molecular Weight:210.23

106-37-6 Synthesis

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Yield:34121-64-7 91%

Reaction Conditions:

Stage #1: 1.4-dibromobenzene;tetrakis(triphenylphosphine) palladium⁽⁰⁾ for 0.25 h;
Stage #2: 2-(tributylstannyl)furan at 100; for 24 h;

Steps:

3

2-(4-Furan-2-yl-phenyl)-furan (15); To a stirred solution of 1,4-dibromobenzene (5 mmol) was added palladium tetrakis-triphenylphosphine (400 mg). The reaction mixture was kept stirring for 15 min after which 2-tributylstannylfuran (10 mmol) was added and the reaction mixture was refluxed at 100 °C for 24 h. The solvent was then evaporated to dryness to give a dark brown residue that was suspended in water and extracted with CH₂Cl₂. The organic layer was passed over hyflo, dried (Na₂SO₄) and evaporated to dryness under reduced pressure to give 15 in 91% yield; mp 149-150 °C. ¹H NMR (DMSO-d₆); δ 6.62 (d, 2H), 7.01 (d, 2H), 7.76-7.79 (m, 6H). MS (ESI) m/e (rel. int.): 210 (M⁺, 100), 181 (40), 153 (30). Anal. Calc. for C₁₄H₁₀O₂: C% 79.98; H% 4.79; Found C% 80.12; H% 4.59.