ChemicalBook CAS DataBase List Benzonitrile, 4,4'-(2,5-thiophenediyl)bis-

Benzonitrile, 4,4'-(2,5-thiophenediyl)bis- synthesis

5synthesis methods

Product Name:Benzonitrile, 4,4'-(2,5-thiophenediyl)bis-
CAS Number:55368-38-2
Molecular formula:C18H10N2S
Molecular Weight:286.35

3141-27-3 Synthesis

3141-27-3
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126747-14-6 Synthesis

126747-14-6
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Benzonitrile, 4,4'-(2,5-thiophenediyl)bis-

55368-38-2
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Yield:55368-38-2 94%

Reaction Conditions:

with palladium diacetate;sodium carbonate;triphenylphosphine in 1,2-dimethoxyethane;water at 80; for 2 h;Inert atmosphere;Microwave irradiation;

Steps:

5.1.2. 4,4'-Thiene-2,5-diyldibenzonitrile (2)

A reaction vessel containing a solution of Pd(OAc)₂ (20 mg, 0.09 mmol) and PPh₃ (94.5 mg, 0.36 mmol) in DME (9 mL) was stirred for10 min under Ar atmosphere. Following, 2,5-dibromothiophene (0.1 mL, 0.89 mmol) and 2 M Na₂CO₃ (1.6 mL, 3.2 mmol) were added. After 5 min, 4-cyanophenylboronic acid (290 mg, 1.97 mmol) was added, and the mixture was stirred for 2 h at 80 °C in a MW reactor. The solvent was then removed under reduced pressure, and the reaction mixture was suspended in dichloromethane (DCM), transferred to a separation funnel, and washed well with saturated Na₂CO₃ solution (2 × 25 mL) containing 1 mL NH₃. The organic layer was collected, dried with anh. Na₂SO₄, and the solvent was filtered. Subsequently, the solvent was removed under reduced pressure and intermediate 2 was isolated using column chromatography (dry-flash, SiO₂, eluent DCM), and collected as a pale yellow amorphous powder. The yield was 240 mg (94%, mp = 282-284 °C) [21]. IR (KBr): 2925w, 2359w, 1535m, 1506m, 1380w, 1207s, 1150s, 1035s, 825s, 781m, 732m, 702m cm^-1. ¹H NMR (200 MHz, CD₃OD): 7.80-7.60 (m, 8H-Ar), 7.50-7.45 (s, H-C(3) and H-C(4)). ¹³C NMR (50 MHz, CD₃OD): 143.31, 137.90, 132.88, 126.36, 125.98, 118.64, 111.19. HPLC purity: method A, RT 15.397 min, area 99.03%; method B: RT 14.656 min, area 96.58%.

References:

Opsenica, Igor;Filipovic, Vuk;Nuss, Jon E.;Gomba, Laura M.;Opsenica, Dejan;Burnett, James C.;Gussio, Rick;Solaja, Bogdan A.;Bavari, Sina [European Journal of Medicinal Chemistry,2012,vol. 53,p. 374 - 379] Location in patent:experimental part

18245-28-8 Synthesis