ChemicalBook CAS DataBase List 5-P-TOLYL-THIOPHENE-2-CARBALDEHYDE

5-P-TOLYL-THIOPHENE-2-CARBALDEHYDE synthesis

10synthesis methods

Product Name:5-P-TOLYL-THIOPHENE-2-CARBALDEHYDE
CAS Number:38401-68-2
Molecular formula:C12H10OS
Molecular Weight:202.27

4701-17-1 Synthesis

4701-17-1
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38401-68-2
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Yield: 88%

Reaction Conditions:

with dichloro bis(acetonitrile) palladium(II);sodium carbonate in ethanol;water at 45 - 50;Suzuki-Miyaura Coupling;

Steps:

Synthesis of 5-arylthienyl-2-carbaldehyde (2a-e). General procedure.
General procedure: A mixture of aryl boronic acid(s) (3.2 mmol), sodium carbonate (0.31g, 2.9 mmol), acetonitrile-dichloro palladium (II) (0.02g, 0.077mmol) and 5-bromothiophene-2-carbaldehyde (1) (0.3 mL, 2.61 mmol), were dissolved in H2O (6 mL) and ethanol (3 mL). The reaction mixture was stirred and heated at (45-50 oC) for 10-12 hours. The resulting black solution was poured into cooled water and extracted with ethyl acetate (4 × 15 mL). The organic layer was dried over anhydrous Na2SO4, filtered and evaporated under vacuum. The solid product was collected then column chromatographed (petroleum ether: ethyl acetate, 10:1) and crystallized from petroleum ether-benzene mixture (1:1). 5-(4-Methylphenyl)thiophene-2-carbaldehyde (2a). It was obtained as pale yellow crystals from petroleum ether (0.662 g), 88 % yield, mp 96-97 C41. IR (cm-1): 1660 (CHO). 1H-NMR (CDCl3): 9.90(s,1H, CHO), 7.76-7.25 (m, Ar-H), 2.42 (s, 3H, CH3). 13C-NMR (CDCl3): 184.98, 155.98, 146.08, 143.25, 141.72, 132.95, 131.66, 130.98, 130.61, 127.63, 21.23. Ms (EI): m/z for C12H10OS; (2002) Calcd C, 71.25; H, 4.98; O, 7.91; S, 15.85 % Found: 71.05; H, 4.79; O, 7.76; S, 15.81 %

References:

Elghamry, Ibrahim;Abdelsalam, Mamdouh;Al-Faiyz, Yasair;Al-Gadry, Meshail;Al-Taysan, Norah [Arkivoc,2021,vol. 2020,p. 322 - 337]

98-03-3 Synthesis