Sodium Carbonate → 2,5-Bis(3',4'-dimethoxyphenyl)thiophene

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,5-dibromothiophene (14) (242 mg, 1 mmol), (3,4-dimethoxy phenyl)boronic acid (15) (455 mg, 2.5 mmol), and Pd(PPh3)4 (58 mg, 0.05 mmol) in dioxane (10 mL) was added Na2CO3 (12 mL, 2.0 M aqueous solution). The resultant mixture was purged with nitrogen and stirred rapidly while heating at 90° C. overnight. The reaction mixture was cooled to 23° C., acidified with 1M HCl and extracted with EtOAc. The combined organic extracts were washed with H2O, dried over MgSO4, filtered and concentrated under reduced pressure. 2,5-bis(3′,4′-dimethoxyphenyl)thiophene (16) was obtained quantitatively as a green-yellow solid after the purification by column chromatography (10%-20% EtOAc in hexanes).

Provenance & Evidence