4-[2-(4-Hydroxyphenyl)propan-2-yl]phenol (200 mg, 876 μmol, 1.00 equiv), 4-azido-2,3,5,6-tetrafluorobenzoic acid (433 mg, 1.84 mmol, 2.10 equiv), and dichloromethane (25 mL) were placed in a 100 mL round-bottom flask, and the mixture was cooled to 0 °C. To the mixture were added N,N-dimethylpyridin-4-amine (10.7 mg, 87.6 μmol, 0.100 equiv) and N,N'-diisopropylcarbodiimide (221 mg, 1.75 mmol, 2.00 equiv), and then the mixture was warmed to 21 °C and stirred for 24 h. After quenching with 1 N HCl (20 mL), the organic phase was washed with water (100 mL) and saturated NaHCO3 (aq) (50 mL), and was dried over anhydrous sodium sulfate. The solvent was removed by evaporation. The crude product was purified by silica gel column chromatography eluting with cyclohexane/dichloromethane (20 : 1) to give propane-2,2-diylbis(4,1-phenylene) bis(4-azido-2,3,5,6-tetrafluorobenzoate) (379 mg, 572 μmol, 65% yield) as a colorless solid.
