General procedure: 4-Iodobenzoic acid (15.62 g, 63 mmol, 1.05 eq.) was suspended in anhydrous DMF (90 mL, 6 vol.) under nitrogen protection, potassium carbonate (8.7 g, 63 mmol, 1.05 eq.) was added, and stirred for 10 minutes. Subsequently, benzyl bromide (10.25 g, 7.13 mL, 60 mmol, 1 eq.) was slowly added dropwise for a controlled time of about 5 minutes. The reaction mixture was continued to be stirred at room temperature for 6.25 hours. Upon completion of the reaction, the mixture was transferred to a partition funnel and extracted with ether (200 mL) and water (200 mL) by partition. The aqueous phase was extracted once more with ether, and the organic phases were combined and washed sequentially with water, aqueous lithium chloride and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford benzyl 4-iodobenzoate (18.38 g, 86% yield) as a white crystalline solid. The product was analyzed by LCMS: tRET = 3.81 min, 70% ES + ve 376,356 (artifactual peak appeared at 1.48 min, 28%).1H NMR (400 MHz, DMSO-d6) δ ppm: 7.92 (d, 2H), 7.74 (d, 2H), 7.46 (d, 2H), 7.35-7.42 (m, 3H ), 5.34 (s, 2H).
