Ammonium Chloride → HCID 90070482, compound

Participants

Reaction Conditions

Reaction Steps

2-(3-Bromophenyl)-6,6-dimethyl-6,7-dihydrobenzo[b]thiophen-4(5H)-one (0.36 g, 1.0 mmol) was dissolved in anhydrous THF (10 mL) and the solution was cooled to −30° C. under a nitrogen atmosphere. Vinyl magnesium chloride (2.8 mL, 1.6 M solution in THF, 5.4 mmol) was added to the ketone portion-wise whilst maintaining the temperature at −30° C. Upon completion of the addition, the reaction was allowed to warm to 25° C. and then stirred for 18 hr. Monitoring of the reaction by LC/MS indicated starting material was still present so further vinyl magnesium chloride (2.8 mL, 1.6 M solution in THF, 5.4 mmol) was added. After 2 hr the solution was treated with saturated aqueous ammonium chloride solution. The product was extracted into ethyl acetate (×3) and this was back extracted with water and saturated brine. The organic extracts were combined, dried (MgSO4), filtered and concentrated in vacuo to afford the title compound (0.43 g, quant.).

Provenance & Evidence