FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[CH:14]([CH3:16])[CH3:15])(=O)=O.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.CS(C)=O.[C:59]([O:62][CH2:63]C)(=[O:61])C>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C:59]([O:62][CH3:63])=[O:61])=[C:8]([CH:14]([CH3:16])[CH3:15])[CH:9]=1A mixture of 4-bromo-2-isopropylphenyl trifluoromethanesulfonate (0.705 g), palladium acetate (0.0228 g), 1,3-bis-(diphenylphosphino)propane (0.0419 g) and triethylamine (0.628 mL) in methanol (6 mL)/dimethylsulfoxide (9 mL) was stirred at 55° C. overnight under an atmosphere of carbon monoxide. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: diethyl ether/n-hexane=1/10) to afford methyl 4-bromo-2-isopropylbenzoate (0.355 g).
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