[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.N1C=CC=CC=1.[CH2:23](O)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>ClCCl.CN(C)C=O>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:7])=[CH:4][CH:3]=1Under a nitrogen atmosphere, 4-iodobenzoic acid (1a) (10.6 g, 42.9 mmol) was dissolved in anhydrous dichloromethane (140 mL), and several drops of anhydrous N,N-dimethylformamide were added. Thereafter, oxalyl chloride (4.50 mL, 42.4 mmol) was added at 0° C., and the mixture was stirred at room temperature for 10 hr. The solvent was removed, anhydrous pyridine (70 mL) and n-heptanol (7.0 mL, 49.4 mmol) were added, and the mixture was stirred at 70° C. for 5 hr. The reaction solvent was removed, the residue was diluted with ethyl acetate, washed with distilled water and saturated aqueous sodium hydrogen carbonate solution, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (ethyl acetate:hexane=1:19) to give heptyl 4-iodobenzoate (2a) (14.5 g, yield 97%) as an oily liquid.
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