Bromide ion → HCID 19606301, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of magnesium (0.304 g, 12.6 mmol) in dry tetrahydrofuran (5 ml) with a iodine crystal was added drop by drop and under inert atmosphere with a solution of 2-bromoethylbenzene (1.72 ml, 12.6 mmol) in dry tetrahydrofuran (12 ml). The reaction, started during the bromide addition, was left at room temperature for 2.5 h. After that a solution of CuBr.(CH3)2S (163 mg, 0.79 mmol) in tetrahydrofuran (2 ml) and a solution of 2-chromanemethyl trifluoromethanesulfonate (1.381 g, 4.67 mmol) in tetrahydrofuran (5 ml) were added successively at 0° C. and the mixture was left under stirring at 0° C. for 2.5 h. After this time, the mixture was poured slowly onto a mixture of dichloromethane (25 ml) and an ammonium chloride saturated aqueous solution (20 ml). The phases were separated and the aqueous phase was extracted with dichloromethane (4×25 ml). The combined organic extracts were dried and the solvent was evaporated off under reduced pressure, to obtain a crude which was purified by chromatography through a silica gel column, eluting with hexane:dichloromethane, 9:1, to recover 0.990 g of the title product (85% yield).

Provenance & Evidence