3-Bromothiophene → 3-(Diethoxyphosphoryl)thiophene

Participants

Reaction Conditions

Reaction Steps

Under nitrogen, 0.0815 g (0.5 mmols) of 3-bromothiophene and 0.0231 g (0.02 mmols) of commercially available tetrakistriphenylphosphine palladium were dissolved in DMF, to which 0.0829 g (0.6 mmols) of commercially available diethyl phosphite and 0.0776 g (0.6 mmols) of diisopropylethylamine were added at room temperature. Thereafter, the reaction mixture was heated to 110° C. and stirred for 4 hours. After the reaction, the reaction mixture was cooled down to room temperature, to which a disodium hydrogen phosphate/sodium dihydrogen phosphate buffer solution, adjusted to pH=7, was added to the reaction mixture, followed by extraction with ethyl acetate. The organic phase was washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was removed by distilling off under reduced pressure, and the resulting crude product was purified with a silica gel column (ethyl acetate:hexane=1:1) to obtain the specified substance in the form of a yellow oil at a yield of 0.0782 g (yield: 71%).

Provenance & Evidence