反应详情

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.

1. temperaturethe mixture is refluxed under nitrogen for 2 days
2. customThe excess SOCl2 is evaporated under reduced pressure
3. customAfter quenching with 1M HCl solution
4. extractionthe residue is extracted by dichloromethane
5. dry with materialThe mixture is dried over MgSO4
6. custompurified by column chromatography (silica gel, hexane/ethyl acetate=80:1)