Sodium Carbonate → 3-Bromo-2-methoxy-5-phenylthiophene

Participants

Reaction Conditions

Reaction Steps

250 ml of anhydrous THF was added into 24 g (88 mmol) of 3,5-dibromo-2-methoxythiophene and was cooled to be −78° C. with dry ice-methanol. Then, 56 ml (92 mmol) of a solution containing 15% n-butylithium hexane was slowly dripped into it. After being stirred for 1 hour, 32 ml (123 mmol) of tri-n-butyl borate was slowly dripped into it and stirred for 2 hours. After being returned to a room temperature, 90 ml of 20 wt % Na2CO3, 18 g (88 mmol) of iodobenzene, and 4.4 g (0.36 mmol) of Pd(Ph3P)4 were added to the solution and refluxed for 5 hours at 70° C. The reaction solution was extracted with ether, washed with a salt solution, and dried with addition of magnesium sulfate. The dried extract was condensed after removing magnesium sulfate by filtration. By developing the product with hexane on a silica gel column, a colorless solid 3-bromo-2-methoxy-5-phenylthiophene was obtained (Rf=0.35). The yield was 15 g in weight and 63% in percentage.

Provenance & Evidence