2-(Allyloxymethyl)-1-fluoro-3-iodobenzene → 8-Fluoro-4-methylene-3,4-dihydro-1H-isochromene

Participants

Reaction Conditions

Reaction Steps

2-(Allyloxymethyl)-1-fluoro-3-iodobenzene (1 g) was dissolved in 20 mL of CH3CN and 2.4 mL of Et3N. The reaction solution was vacuum degassed three times, followed by the addition of Pd(OAc)2 (37.6 mg) and PPh3 (89.8 mg). The resulting mixture was heated at 80° C. for 16 hours. The reaction mixture was cooled to room temperature and diluted with Et2O. The organic layer was washed with 1N HCl, 10% aqueous NaHCO3, brine, and then dried over Na2SO4. After filtration, the filtrate was concentrated to dryness to offer a brown oil, which was purified by flash chromatography to offer 200 mg of the title compound.

Provenance & Evidence