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

Temperature

80 °C

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.

1. customdegassed three times
2. additionfollowed by the addition of Pd(OAc)2 (37.6 mg) and PPh3 (89.8 mg)
3. temperatureThe reaction mixture was cooled to room temperature
4. additiondiluted with Et2O
5. washThe organic layer was washed with 1N HCl, 10% aqueous NaHCO3, brine
6. dry with materialdried over Na2SO4
7. filtrationAfter filtration
8. concentrationthe filtrate was concentrated to dryness
9. customwas purified by flash chromatography

ORD record

ord-08a3243dffae4a92b68a2013447876a7

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915268B2