Potassium Iodide → Methyl 3-hydroxy-4-iodobenzoate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 4-amino-3-hydroxybenzoate (1 eq.) in THF was diluted with aqueous HCl 3N and cooled to 0° C. Sodium nitrite (1.1 eq.) in H2O was added over 5 min. The reaction mixture was stirred for 25 min at 0° C. and then a solution of potassium iodide (4 eq.) in H2O was added in one portion, and stirred for 15 min. The reaction mixture was partitioned between water and EtOAc, the organic layer was washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with DCM) to afford methyl 3-hydroxy-4-iodobenzoate.

Provenance & Evidence