[CH3:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].I[C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1>C(O)CCC.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]
3-Methyl-4-methoxyphenylboronic acid (542 mg) was combined with 4-iodobenzoic acid (810 mg), cesium carbonate (5.32 g), toluene (16 mL), water (8 mL) and n-butanol (4 mL). The mixture was degassed under vacuum with argon purging after which, tetrakis-triphenylphosphine palladium (38 mg) was added. The reaction was heated to 80° C. for 20 hours after which, it was cooled to room temperature and diluted with ethyl acetate (16 mL). The layers were separated and the organics were concentrated to dryness. The residue was purified on silica gel (50% to 100% ethyl acetate/hexane over 40 minutes) giving 3′-methyl-4′-methoxy-4-biphenylcarboxylic acid (240 mg). Yield=30%
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