Hydrochloric Acid → 5-bromo-1-(1,3-dithian-2-yl)-2,3-dihydro-1H-inden-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,3-dithiane (1.82 g, 14.7 mmol) in dry THF (20 ml) was added n-butyllithium (8.62 ml, 13.8 mmol, 1.6 M in hexane) dropwise at −30° C. The resulting mixture was stirred for 2 h at −15° C. Then, a solution of 5-bromo-2,3-dihydro-1H-inden-1-one (2 g, 9.19 mmol) in dry THF (24 ml) was added dropwise, maintaining the temperature between −15° C. and −6° C. After the addition was completed, the brown solution was allowed to warm to 0° C. and was then stored in the fridge overnight. Then, 1N HCl was added and the brown mixture was extracted two times with diethylether. The combined organic layers were washed with brine, dried with Na2SO4 and evaporated. The remaining residue was purified by chromatography (silica gel; heptane/EtOAc 90:10-75:25) to obtain the title compound as light yellow gum (2.167 g, 71%). MS: 330.1 [M+H]+.

Provenance & Evidence