Iodine → 8-(4-Bromophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

Participants

Reaction Steps

To a flask charged with dry, freshly ground magnesium turnings (187 mg, 7.7 mmol) and I2 (81 mg, 0.32 mmol) in THF (10 mL) was added a solution of 1,4-dibromobenzene (1.81 g, 7.7 mmol) in THF (10 mL) slowly. The resulting mixture was stirred at rt for 30 min. The resultant pale yellow Grignard solution was cooled to −78° C. and to it was added a solution of 1,4-dioxaspiro[4.5]decan-8-one (1 g, 6.4 mmol) in THF (10 mL) slowly dropwise. The reaction was stirred at −78° C. for 20 min before being allowed to stir and warm to rt for 15 hr. The reaction was quenched with a saturated aqueous NH4Cl solution and extracted with methyl tert-butyl ether. The organic phase was washed with a saturated aqueous NaCl solution, dried over MgSO4, filtered and concentrated by rotary evaporation in vacuo to afford 2.2 g of crude orange oil. Purification of the crude material by column chromatography (50 g silica gel, 0-50% EtOAc:Hept, monitor for 225 nm) afforded 0.99 g of the title compound as a white solid.

Provenance & Evidence