Triethylamine → HCID 15485563, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-bromo-2-(4-hydroxyphenyl)benzo[b]-thiophene (9.4 g, 30.8 mmol) in 50 mL of dry DMF was treated with Et3N (6.3 g, 61.6 mmol) and cooled to 0° C. To this was added in a dropwise manner 14.2 g (46.2 mmol) triisopropylsilyl trifluoromethanesulfonate. The cooling bath was removed and the reaction allowed to stir at ambient temperature for 2 h before pouring into 100 mL brine. This was extracted with EtOAc (2×50 mL). The combined extracts were washed with brine (2×100 mL), dried over MgSO4 and concentrated under reduced pressure to 4.8 g of an oil. The crude product was purified by chromatography (SiO2 ; hexanes) to recover 11.7 g (25.4 mmol, 82%) of the desired product as a white solid.

Provenance & Evidence