Sodium Carbonate → HCID 10956973, compound

Participants

Reaction Conditions

Reaction Steps

150 ml of anhydrous THF and 6.5 g (23 mmol) of 3,5-dibromo-2-ethoxythiophene was added into a flask under argon atmosphere. Then, 15 ml (25 mmol) of a solution containing 15% n-butylithium hexane was slowly dripped into it at −78° C. After being stirred for 1 hour at −78° C., 9.1 ml (34 mmol) of tri-n-butyl borate was slowly dripped into it and was stirred for 1.5 hours. After being returned to a room temperature and quenched with water, 4.6 g (23 mmol) of iodobenzene, 1.1 g (0.95 mmol) of Pd(PPh3)4, and 50 ml of 20 wt % Na2CO3 aqueous solution was added to the solution and was refluxed overnight at 70° C. The reaction solution was extracted with ether, was washed with a salt solution, and was dried with magnesium sulfate. After filtering out the magnesium sulfate and evaporating the solvent, the product was developed with hexane on a silica column to give 3-bromo-2-ethoxy-5-phenylthiophene (Rf=0.31). The yield was 4.9 g in weight and 76% in percentage.

Provenance & Evidence