Hydrochloric Acid → 5-Bromo-2-(3-furanyl)-3-thiophenecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,5-dibromo-3-thiophenecarboxylic acid (750 mg, 1.38 mmol)[prepared according to Goto, Hiromasa; Dai, Xiaoman; Narihiro, Harunori; Akagi, Kazuo Macromolecules 2004 37, 7, 2353-2362.] in dioxane/H2O (5:1, 6 mL) was added K2CO3 (486 mg, 3.52 mmol), tetrakistriphenylphosphine Pd(0) (51 mg, 44 umol), and 3-furanboronic acid (108 mg, 0.968 mmol). The reaction mixture was heated to 80° C. in a sealed tube. After 12 h, the solution was poured onto H2O (100 mL) and the pH was adjusted to ˜4 with aqueous HCl. The aqueous phase was extracted several times with DCM and the combined organic fractions were dried (Na2SO4), concentrated under vacuum and used directly: LC-MS (ES) m/z=273.

Provenance & Evidence