ChemicalBook CAS DataBase List 5-(4-Fluorophenyl)thiophene-2-carboxylic acid

5-(4-Fluorophenyl)thiophene-2-carboxylic acid synthesis

9synthesis methods

Product Name:5-(4-Fluorophenyl)thiophene-2-carboxylic acid
CAS Number:115933-30-7
Molecular formula:C11H7FO2S
Molecular Weight:222.24

7311-63-9 Synthesis

7311-63-9
338 suppliers
$5.00/250mg

1765-93-1 Synthesis

1765-93-1
557 suppliers
$9.00/1g

5-(4-Fluorophenyl)thiophene-2-carboxylic acid

115933-30-7
71 suppliers
$45.00/50mg

Yield: 71%

Reaction Conditions:

with potassium phosphate;tetrakis(triphenylphosphine) palladium⁽⁰⁾ in N,N-dimethyl-formamide at 105;Inert atmosphere;Suzuki Coupling;

Steps:

4.1.1 Synthesis of substituted 5-phenylfuran/thiophene-2-carboxylic acid (1a-1d) and (7a- 7d)
General procedure: 5-bromofuran-2-carboxylic acid/ 5-bromothiophene-2-carboxylic acid (0.0013mol), substituted boronic acid (0.0015mol), Pd(Ph₃)₄ (10mol %), were added in the a round bottom flask. K₃PO₄ (0.0026mol), and dry 11 DMF (5mL) were added and reaction was performed at 105°C under nitrogen atmosphere for 15-20h. After the completion of reaction, reaction mixture was quenched with cold water (15mL), acidified with HCl (0.5mL), followed by extraction with EtOAc (25×4mL). The combined EtOAc layer was washed with saturated sodium bicarbonate solution (10×2mL) to remove excess of HCl. The EtOAc layer, was filtered through celite bed over cotton, to remove Pd(Ph₃)₄, and concentrated under vacuum. The crude product was adsorbed and loaded on silica gel (100-200 mesh) column. The column was eluted with ethyl acetate (10-20%) in hexane to give desired compound in yield ranging from 43 to 71%.

References:

Kumar, Gautam;Krishna, Vagolu Siva;Sriram, Dharmarajan;Jachak, Sanjay M. [European Journal of Medicinal Chemistry,2018,vol. 156,p. 871 - 884]