Dimethylformamide → 3,5-diiodobenzaldehyde

Participants

Reaction Steps

To a slurry of 1,3,5-triiodobenzene (7.5 G, 16.4 mM) in 72 mL of ether at -78° was added n-butyllithium 7.2 mL; 18 mM). After 15 minutes of stirring, 2.8 mL (36 mM) of N,N-dimethylformamide was added dropwise and the reaction mixture was stirred overnight. After diluting with 100 mL of ethyl acetate, the reaction mixture was washed with 3×50 mL of saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. Solvent removal gave a crude product, which was chromatographed on silica gel (application in minimum amount of CH2Cl2 ; and elution with 1:9 EtOAc:hexane) to yield 1.3 G of the desired aldehyde as cream colored solid.

Provenance & Evidence