Iodine → 2-(Iodomethyl)-2,3-dihydro-1-benzofuran

To a solution of 2-allylphenol (10 g, 75 mmol) in dichloromethane (150 ml) was added SnCl4 (29.7 g, 37.3 mmol, 0.5 eq) and iodine (19 g, 75 mmol, 1 eq) at room temperature. After stirring for 5.5 hours, the reaction mixture was diluted with additional dichloromethane (200 ml) and then quenched with water (200 ml). The organic layer was separated and the aqueous layer was adjusted pH to ˜8 with sodium bicarbonate and then extracted with dichloromethane (3×150 ml). The organic layers were combined, washed with 5% aqueous Na2S2O4 (200 ml), dried over anhydrous magnesium sulfate, filtered, and then concentrated under vacuum. The crude material was purified by silica gel chromatography using with 0.5-1% ethyl acetate in petroleum ether to elute. The product-containing fractions were combined and concentrated to afford 2-(iodomethyl)-2,3-dihydro-1-benzofuran as brown oil (7 g, 36%); 1H NMR (300 MHz, CDCl3): δ 7.09-7.17 (m, 2H), 6.74-6.89 (m, 2H), 4.84-4.93 (m, 1H), 3.30-3.47 (m, 3H), 3.00-3.08 (m, 1H).

1. customquenched with water (200 ml)
2. customThe organic layer was separated
3. extractionextracted with dichloromethane (3×150 ml)
4. washwashed with 5% aqueous Na2S2O4 (200 ml)
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. customThe crude material was purified by silica gel chromatography
9. washto elute
10. concentrationconcentrated

ORD-Eintrag

ord-88043373ac8f4dfeb82b9f2d3271556b

Quelldatensatz

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09249102B2