3-Iodobenzyl alcohol

Synthesis

Methyl m-iodobenzoate (1.0 eq.) was placed in a 100 mL round-bottom flask, a magnetic stir bar was added, oxygen was removed with N2, a rubber stopper was placed, and an N2 balloon was inserted. A suitable amount of dried toluene was added as a solvent using a syringe, and the mixture was stirred until homogeneous. Then, LiBH4(inTHF) (2.0 M, 1.0–2.0 eq.) was added using a syringe. The system was then transferred to an oil bath at 100 °C and reacted for 1 h. TLC was used to confirm the completeness of the reaction. When the reaction was complete, excess 5% dilute hydrochloric acid was slowly added as a quencher until no more bubbles were generated in the reaction system.

Then, the reaction system was nearly completely evaporated by rotary evaporation under reduced pressure, followed by extraction three times with ethyl acetate. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was collected and evaporated under reduced pressure. The crude product was purified by column chromatography (dry loading, eluent: petroleum ether/ethyl acetate = 3/1 (v/v), Rf = 0.400) to obtain a clear, pale yellow liquid, which was the product 3-iodobenzyl alcohol.

Chemical Properties

clear pale yellow to orange-red liquid

Uses

3-Iodobenzyl alcohol was used in the preparation of:

• 6-(3-iodo-benzyloxy)-9H-purin-2-ylamine
• 3-(1-methylethenyl)benzenemethanol
• 3-ethenylbenzenemethanol
• dendritic iron(II) porphyrins

General Description

3-Iodobenzyl alcohol undergoes cross-coupling reaction with zinc reagent to yield 3R-tert-butoxycarbonylamino-4-(3-hydroxymethylphenyl)butanoic acid benzyl ester.