Thionyl Chloride → Chloro-iododibenzoylbenzene

Beteiligte Stoffe

Reaktionsschritte

The 5-chloro-2-iodo-isophthalic acid (product Example 1a, 3.8 g, 12 mmol) is added to SOCl2 (30 mL, excess) and the mixture is refluxed under nitrogen for 2 days. The excess SOCl2 is evaporated under reduced pressure, then the resultant oil containing the 5-chloro-2-iodo-isophthaloyl dichloride (4.2 g, 12 mmol) is dissolved in dichloromethane (50 mL). To this solution, 1-phenyldodecane (10 g, 47 mmol) and AlCl3 (4.7 g, 35 mmol) are added at 0° C. The mixture is stirred from 0° C. to room temperature overnight. After quenching with 1M HCl solution, the residue is extracted by dichloromethane. The mixture is dried over MgSO4 and purified by column chromatography (silica gel, hexane/ethyl acetate=80:1) to afford the chloro-iododibenzoylbenzene as a colorless oil. Yield 2.3 g (27%). FD-MS (8 kV): m/z=727.7. 1H NMR (250 MHz, CDCl3-d) δ ppm 0.88-0.90 (m, 6 H, CH3), 1.26-1.30 (m, 32 H, CH2), 2.69 (t, J=7.3, 4 H, CH2), 7.27-7.41 (m, 6 H, Ar), 7.75 (t, J=7.9, 4 H, Ar); 13C NMR (62.5 MHz, CD2Cl2-d2): 13C NMR (250 MHz, CD2Cl2-d2): δ ppm 14.3, 23.1, 29.7, 29.8, 29.9, 30.0, 31.4, 32.3, 36.5, 128.8, 129.4, 130.9, 132.9, 135.3, 148.2, 151.1, 195.4.

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