Br[CH:2]([C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([CH:2]([O:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]([O:5][CH3:6])=[O:4])=[CH:8][CH:9]=1To a solution of methyl 2-bromo-2-(4-bromophenyl)acetate (9 g, 29.3 mmol) in N,N-dimethylformamide was added phenol (5.5 g, 60 mmol), cesium carbonate (9.5 g, 30 mmol), tetrabutylammonium iodide (1.08 g, 2.93 mmol). The mixture was stirred at 40° C. for 15 hours. Thin layer chromatography showed the start material was consumed completely. Then the mixture was concentrated under vacuum and purified by column chromatography (silica gel, petroleum ether/ethyl acetate=25:1) to give methyl 2-(4-bromophenyl)-2-phenoxyacetate (6 g, 61%).
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