Iodine → 3-(4-Iodomethyl-2-methyl-phenyl)-propionic acid methyl ester

A mixture of 3-(4-Hydroxymethyl-2-methyl-phenyl)-propionic acid methyl ester (0.62 g, 2.98 mmol), triphenyl phosphine (0.86 g, 3.27 mmol) and dichloromethane (10 mL) is stirred at room temperature. A solution of iodine (0.83 g, 3.27 mmol) in benzene (5 mL) is added and the black mixture is stirred at room temperature 2 hr. The brown mixture is diluted with 10% aqueous sodium hydrogen sulfite (5 mL) and the resulting clear mixture is washed with ethyl acetate (3×50 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered and concentrated. The residue is purified via silica chromatography eluting with 9:1 hexanes:ethyl acetate to afford the title compound as a crystalline ivory solid, 0.689, 72%. MS M++1 319. The structure is confirmed by 1H NMR spectroscopy.

1. stirringthe black mixture is stirred at room temperature 2 hr
2. washthe resulting clear mixture is washed with ethyl acetate (3×50 mL)
3. dry with materialThe combined extracts are dried over anhydrous magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue is purified via silica chromatography
7. washeluting with 9:1 hexanes

ORD record

ord-a15d1735130841f6b6b4cbc60f23a5a4

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07153878B2