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The reaction mixture under reflux was thermalized for 2 h, and aliquot samples were removed after 30, 60, and 120 min.
Each sample was weighed and extracted using 50 ml of an ethanol-water (50/50) mixture under reflux [ 25].
With this optimized protocol, the 5,5′-substituted benzothiophene derivative, 5,5′ -BT, was obtain using Pd2 dba 3, [ tBu 3PH]BF4 and K3PO4 as base in a THF and water mixture under reflux condition.
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The mixture was under reflux at 85 °C for 24 h.
To a solution of 1,8-naphthalic anhydride (2.2 mmol) in boiling glacial acetic acid (15 mL), thiosemicarbazide (2.8 mmol) was added and left the mixture stirring under reflux for 1 h.
The reaction mixture was heated under reflux for 1 h.
The resulting mixture was heated under reflux for 3 h.
The reaction mixture was stirred under reflux for 10 h.
The mixture was heated under reflux for 15 h.
The reaction mixture was stirred under reflux under N2 atmosphere for 24 h.
Phosphorous acid, 19.31 g, was added and the mixture was heated under reflux at 90 °C.
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