Benzyl Alcohol → Benzyl 2-amino-3-iodobenzoate

Participants

Reaction Steps

To a solution of 2-amino-3-iodobenzoic acid (5.00 g), benzyl alcohol (2.17 mL) and triphenylphosphine (7.97 g) in tetrahydrofuran (76 mL) was added a 40% toluene solution (13.2 g) of diethyl azodicarboxylate, and the mixture was stirred at room temperature for 0.5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-15:85) to give the title compound (5.56 g, yield 83%) as an orange oil. MS m/z 354 (M+H+).

Provenance & Evidence