ChemicalBook CAS DataBase List 2-(4-Fluorophenyl)-thiophene

2-(4-Fluorophenyl)-thiophene synthesis

11synthesis methods

Product Name: 2-(4-Fluorophenyl)-thiophene
CAS Number:58861-48-6
Molecular formula:C10H7FS
Molecular Weight:178.23

2-(4-Fluorophenyl)thiophene is an important intermediate in the synthesis of antidiabetic drug Canagliflozin. It can be synthesized by 5-(4-fluorophenyl)thiophene-2-carboxylic acid under the catalysis of copper powder was heated and decarboxylation.

1003-09-4 Synthesis

1003-09-4
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$10.00/25g

1765-93-1 Synthesis

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

58861-48-6
358 suppliers
$8.00/1g

Yield:58861-48-6 85%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium carbonate in N,N-dimethyl-formamide at 120; for 15 h;Inert atmosphere;

Steps:

4.1 1. Preparation of 2- (4-fluorophenyl) thiophene
A solution of 4.98 g (36 mmol) of 4-fluorobenzeneboronic acid, 4.1 g (30 mmol) of 2-bromothiophene and 10.98 g (60 mmol) of anhydrous potassium carbonate was dissolved in 20 mL of DMF and 24 mg (0.5% (Diphenylphosphino) ferrocene] palladium dichloride, heated to 120 ° C under nitrogen protection, quenched by constant temperature for 15 h, quenched by adding 30 mL of distilled water, treated with 30 mL CH₂Cl₂Extracted twice, the combined organic phase, anhydrous Na₂SO₄Dried and evaporated to dryness. The residue was diluted with petroleum ether and the filtrate was filtered to obtain a pale green filtrate. The filtrate was evaporated to dryness. The residue was purified by silica gel column chromatography using petroleum ether as eluent to give 2- (4-fluorophenyl) Thiophene 4.50 g, the yield was 85%.

References:

Shaanxi Normal University;Li, Baolin;Cui, Yi;Li, Xiabing;Wang, Wei CN106748970, 2017, A Location in patent:Paragraph 0098; 0099; 0100

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6165-68-0 Synthesis