Triethylsilane → 6-Bromo-1,2,3,4-tetrahydronaphthalene

Participants

Reaction Steps

To 7.50 g of 7-bromo-3,4-dihydronaphthalen-1(2H)-one in trifluoroacetic acid (60 ml), 15.5 g of triethylsilane was added dropwise over 30 minutes at room temperature (the temperature of the reaction solution exothermically elevated from 27° C. to 50° C.). After the dropwise addition, the reaction solution was allowed to react at room temperature for 2 hours and then on a water bath at 50° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was poured into 400 ml of saturated aqueous sodium hydrogen carbonate, extracted with ethyl acetate (200 ml×1, 100 ml×1). The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane) to obtain 6.63 g of the desired product (yield 94%).

Provenance & Evidence