Thiophene → MFCD18262442

Participants

Reaction Conditions

Reaction Steps

To a solution of thiophene (252 mg, 2.99 mmol) in THF (3.5 mL) at −78° C. was added n-butyllithium (2.5M, 1.3 mL, 3.2 mmol) dropwise to keep the temperature below −70° C. The solution was stirred for 40 minutes at −78° C. A solution of N-fluorobenzenesulfonimide (987 mg, 3.1 mmol) in THF (5 mL) was added over a period of 20 minutes. The temperature of the mixture was allowed to rise to −10° C. and was subsequently cooled to −78° C. To the mixture was added n-butyllithium (2.5M, 1.3 mL, 3.2 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (580 mg, 3.1 mmol) in THF (2 mL). The reaction was allowed to continue at −78° C. for 30 min and then quenched with saturated aqueous ammonium chloride (10 mL). The organic layer was separated and the aqueous phase was extracted with EtOAc (3×15 mL). The organic layers were combined and dried over sodium sulfate. After removal of solvent, the residue was purified by flash chromatography (petroleum ether/ethyl acetate=20:1) to give the title compound (143 mg, 21%). 1H NMR (400 MHz, CDCl3) δ ppm 1.32 (s, 12H), 6.55 (d, J=3.6 Hz, 1H), 7.27 (d, J=3.6 Hz, 1H).

Provenance & Evidence