3-Bromothiophene → 3-(Diethoxyphosphoryl)thiophene

Temperature

110 °C

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%).

1. additionwere added at room temperature
2. customAfter the reaction
3. additionwas added to the reaction mixture
4. extractionfollowed by extraction with ethyl acetate
5. washThe organic phase was washed with a saturated saline solution
6. dry with materialdried over anhydrous sodium sulfate
7. customThe solvent was removed
8. distillationby distilling off under reduced pressure
9. customthe resulting crude product was purified with a silica gel column (ethyl acetate:hexane=1:1)
10. customto obtain the specified substance in the form of a yellow oil at a yield of 0.0782 g (yield: 71%)

ORD record

ord-baee0fa70c764cc18f46ec80401ab7cb

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030438B2