[I:1][C:2]1[C:3](O)=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:13]([O-:16])([O-])=O.[K+].[K+].BrC[CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C)C=O.C(OCC)(=O)C>[C:26]([Si:23]([CH3:25])([CH3:24])[O:22][CH2:21][CH2:13][O:16][C:5]1[C:4]([O:10][CH3:11])=[CH:3][C:2]([I:1])=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:29])([CH3:28])[CH3:27]
To a solution of 5-iodovanillin (10 g, 35.9 mmol) (Aldrich) in N,N-dimethylformamide (150 mL) was added anhydrous K2CO3 (14.9 g, 108 mmol), and (2-bromo-ethoxy)-tert-butyl-dimethyl-silane (10.3 g, 43 mmol, Aldrich). The reaction mixture was heated at 60° C. for 18 h. The crude was cooled to room temperature, diluted with ethyl acetate, washed with water, brine. The organic layer was separated, dried over MgSO4, concentrated, and purified by chromatography to give 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-iodo-3-methoxy-benzaldehyde as a yellow oil (Yield 15 g, 96%).
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