3-(PERFLUOROOCTYL)PROPYL IODIDE

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 500 mL 2-neck flask equipped with thermometer and gas inlet charged with potassium carbonate (27.6 g), hydroxy benzaldehyde (13.4 g), and 3-(perfluorooctyl)propyl iodide (58.8 g) in DMF (200 mL) was heated to 65° C. (internal temperature). The mixture was stirred at 65° C. until the reaction was complete. The reaction mixture was cooled to room temperature. Water (300 mL) and ether (300 mL) were added and the mixture stirred vigorously for 5 min. The layers were separated and the organic layer retained. The aqueous layer was extracted with ether (3×200 mL). The combined organic layers were washed with water (2×100 mL), Na2S2O3 (1×100 mL), 2.5 N NaOH (3×100 mL), and aqueous NaCl (1×100 mL). The organic layer was dried over MgSO4, filtered and concentrated. The product was further dried under high vacuum for 5 h to give desired product (53 g, 91% yield). The structure of the product was characterized 1H NMR. A 500 mL 2-neck flask equipped with thermometer and gas inlet The reaction mixture was cooled to room temperature the mixture stirred vigorously for 5 min The layers were separated The aqueous layer was extracted with ether (3×200 mL) The combined organic layers were washed with water (2×100 mL), Na2S2O3 (1×100 mL), 2.5 N NaOH (3×100 mL), and aqueous NaCl (1×100 mL) The organic layer was dried over MgSO4 filtered concentrated The product was further dried under high vacuum for 5 h

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (E)-Methyl 3-(4-hydroxyphenyl)acrylate (166 mg, 0.93 mmol) was added to dry DMSO (10 mL) and stirred under nitrogen in a round bottom flask. Crushed sodium hydroxide (44 mg, 1.1 mmol) was added. After 30 minutes, 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-11-iodoundecane (500 mg, 0.85 mmol) was added. The reaction was allowed to stir overnight. Washed with water and extracted with dichloromethane to yield an oil. This crude product was purified on a silica column using hexanes with increasing amounts of ethyl acetate as the eluent. A white solid was isolated (418 mg, 77% yield). 1H NMR (400.14 MHz, CDCl3) δ 7.65 (d, J=16.0 Hz), 7.48 (d, J=8.75 Hz, 2H), 6.90 (d, J=8.75 Hz, 2H), 6.32 (d, J=16.0 Hz), 4.07 (t, J=5.90 Hz, 2H), 3.80 (3H), 2.40-2.20 (m, 2H), 2.18-2.05 (m, 2H). to stir overnight Washed with water extracted with dichloromethane to yield an oil This crude product was purified on a silica column A white solid was isolated (418 mg, 77% yield)

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 500 mL 2-neck flask equipped with thermometer and gas inlet charged with potassium carbonate (27.6 g), hydroxy benzaldehyde (13.4 g), and 3-(perfluorooctyl)propyl iodide (58.8 g) in DMF (200 mL) was heated to 65° C. (internal temperature). The mixture was stirred at 65° C. until the reaction was complete. The reaction mixture was cooled to room temperature. Water (300 mL) and ether (300 mL) were added and the mixture stirred vigorously for 5 min. The layers were separated and the organic layer retained. The aqueous layer was extracted with ether (3×200 mL). The combined organic layers were washed with water (2×100 mL), Na2S2O3 (1×100 mL), 2.5 N NaOH (3×100 mL), and aqueous NaCl (1×100 mL). The organic layer was dried over MgSO4, filtered and concentrated. The product was further dried under high vacuum for 5 h to give desired product (53 g, 91% yield). The structure of the product was characterized 1H NMR. A 500 mL 2-neck flask equipped with thermometer and gas inlet The reaction mixture was cooled to room temperature the mixture stirred vigorously for 5 min The layers were separated The aqueous layer was extracted with ether (3×200 mL) The combined organic layers were washed with water (2×100 mL), Na2S2O3 (1×100 mL), 2.5 N NaOH (3×100 mL), and aqueous NaCl (1×100 mL) The organic layer was dried over MgSO4 filtered concentrated The product was further dried under high vacuum for 5 h