[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:17])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:12]1[C:13]2[C:7]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[O:1][C:8]=2[C:9]([NH:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:11]=1The mixture of N-(2-phenoxyphenyl)acetamide (120 g, 528 mmol), potassium carbonate (7.30 g, 52.8 mmol), palladium acetate (11.85 g, 52.8 mmol) and pivalic acid (539 g, 5280 mmol) was prepared and heated at 105° C. (inner temperature) under air for two days. GC-MS showed 60% product. The reaction was stirred at 115° C. (inner temperature) for another night. The reaction was then cooled to room temperature and neutralized by saturated sodium carbonate solution, which was then extracted by EtOAc three times. The extraction was concentrated to give the crude product N-(dibenzo[b,d]furan-4-yl)acetamide (90 g, 76% yield) as brown solid.
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