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Comparative Example 1; Compound No. 10: Synthesis of: 4-phenyl ethynyl phthalic anhydride 10 by Using the Method as Described in the Above-Described Patent Document No. 3 (JP-A No. 2003-73372); In accordance with the method as described in Patent Document No. 3, 4-phenyl ethynyl phthalic anhydride was synthesized from 4-bromophthalic anhydride and phenyl acetylene. The resultant 4-phenyl ethynyl phthalic anhydride was yellowish brown crystalline powder. The yield thereof was 79.1percent. Physical properties were as follows (measurement conditions were the same as those in Example 3): Melting point: 149.1 to 149.8° C.; Turbidity: 8.1 ppm; Visible light absorption: 0.058 (400 nm), 0.015 (450 nm); and GC purity: 97.5percent.; Comparative Example 2; Synthesis of 4-phenyl ethynyl phthalic anhydride by Using the Method as Described in the Above-Described Patent Document No. 2; In accordance with the method as described in Example 1 of Patent Document No. 2 (JP-A No. 11-180970), 4-phenyl ethynyl phthalic anhydride was synthesized from 4-bromophthalic anhydride and phenyl acetylene. The resultant 4-phenyl ethynyl phthalic anhydride was pale yellow crystalline powder. Physical properties were as follows (measurement conditions were the same as those in Example 3). The yield of the product was 82.3percent: Melting point: 151.1 to 151.8° C.; Turbidity: 10.5 ppm; Visible light absorption: 0.050 (400 nm), 0.022 (450 nm); and GC purity: 98.7percent;. Comparative Example 3; Synthesis of 4-phenyl ethynyl phthalic anhydride by Using the Method as Described in Non-Patent Document No. 2; In accordance with the method as described in Non-Patent Document No. 2 (Polymer, vol. 35, pp. 4858, 1994), 4-phenyl ethynyl phthalic anhydride was synthesized from 4-bromophthalic anhydride and phenyl acetylene. The resultant 4-phenyl ethynyl phthalic anhydride was pale yellow crystalline powder. Physical properties were as follows (measurement conditions were the same as those in Example 3). The yield of the product was 70.6percent: Melting point: 150.5 to 151.1° C.; Turbidity: 12.1 ppm; Visible light absorption: 0.049 (400 nm), 0.023 (450 nm); and GC purity: 98.8percent.
With triethanolamine; acetic anhydride; In pyridine; methanol; ethyl acetate;
Step 1: To a solution of <strong>[120351-94-2]3-(2-aminoethoxy)benzonitrile</strong> (276 mg, 1 mmol, 1.0 equiv) in 5 mL of methanol at room temperature was added TEA (630 muL, 4.5 equiv) and 4-bromophthalic anhydride (227 mg, 1.0 equiv). After stirring at room temperature for 3 h, the solvent was evaporated and the residue was vacuum dried. The residue in 10 mL of pyridine was then treated with 12 mL of acetic anhydride at room temperature overnight. The volatile solvent was evaporated, and the residue was taken up with EtOAc, washed with H2O, dried over MgSO4 and column purified with 1:3 EtOAc/hexanes on silica gel to give 3-[2-(5-bromo-1,3-dioxoisoindolin-2-yl)ethoxy]benzonitrile in 84% yield. LRMS found for C17H12BrN2O3 (M+H)+: 371.05.
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