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Into a solution of benzyl 2,4-dichloro-5-iodonicotinate (3.7 g, 9.1 mmol) in THF (20 mL) was added a solution of sodium benzoxide in THF (1.0 M×20 mL, 20 mmol). The mixture was stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl. The mixture was extracted with ethyl acetate. The organic layers were combined and washed with brine, dried over sodium sulfate, evaporated and purified by silica chromatography (0-7% ethyl acetate in hexanes) to give benzyl 2,4-bis(benzyloxy)-5-iodonicotinate (2.55 g, 51%).

1. customThe reaction was quenched with saturated NH4Cl
2. extractionThe mixture was extracted with ethyl acetate
3. washwashed with brine
4. dry with materialdried over sodium sulfate
5. customevaporated
6. custompurified by silica chromatography (0-7% ethyl acetate in hexanes)