Iodine → HCID 19886356, compound

To a solution of 4-fluoro-2-(prop-2-en-1-yl)phenol (5 g, 32.9 mmol) in dichloromethane (125 mL) was added SnCl4 (4.28 g, 16.5 mmol) and iodine (8.36 g, 32.9 mmol) at room temperature. After an additional 18 hours, the reaction was quenched with water (150 ml) and the pH value was adjusted to 8 with aqueous NaOH solution (2N). The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×100 mL). The combined organic layer was washed with Na2S2O4 (3×100 mL, 5%) to remove iodine and dried over anhydrous magnesium sulfate. The solution was filtered and then concentrated under vacuum. The crude residue was purified by a silica gel column, eluted with 0.5-1% ethyl acetate in petroleum ether to afford 5-fluoro-2-(iodomethyl)-2,3-dihydro-1-benzofuran as a yellow oil (5 g, 54%); 1H NMR (300 MHz, DMSO): δ 7.03-7.08 (dd, J=5.7 Hz, 8.4 Hz, 1H), 6.93-6.86 (dt, J=2.7 Hz, 8.7 Hz, 1H), 6.76-6.70 (m, 1H), 4.88-4.79 (m, 1H), 3.49-3.60 (m, 2H), 3.41-3.32 (dd, J=7.2 Hz, 16.5 Hz, 1H), 2.96-2.88 (dd, J=7.2 Hz, 16.5 Hz, 1H).

1. customthe reaction was quenched with water (150 ml)
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with dichloromethane (2×100 mL)
4. washThe combined organic layer was washed with Na2S2O4 (3×100 mL, 5%)
5. customto remove iodine
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationThe solution was filtered
8. concentrationconcentrated under vacuum
9. customThe crude residue was purified by a silica gel column
10. washeluted with 0.5-1% ethyl acetate in petroleum ether

ORD record

ord-025ee05f005743fbaa407ff7069e3282

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249102B2