p-Diiodobenzene → HCID 14319461, compound

Temperature

70 °C

A 100 ml Schlenk flask equipped with a stir bar was flame-dried and then charged with 1,4-diiodobenzene (3.30 g, 10 mmol), Cu powder (5.08 g, 80 mmol), and 2,2′-bipy (156 mg, 1 mmol). The flask was evacuated and back-filled with argon three times. Anhydrous dimethylsulfoxide (30 mL) was added via a syringe. Perfluorohexyl iodide (6.5 mL, 30 mmol) was added dropwise while stirring. Upon completion of addition, the reaction mixture was heated to 70° C. for 72 hours then removed from heat. The reaction mixture was poured into 100 mL H2O/100 mL diethyl ether and stirred vigorously for 30 min. Solid residues were removed by filtration, and the organic layer was washed twice with dilute NH4OH solution, twice with water, dried over MgSO4. The solvent was removed by evaporation under reduced pressure, and the resulting off-white solids were subjected to sublimation to give S5 as white solids (5.61 g, 78%). 1H NMR (300 MHz, CDCl3): δ 7.77 (s, 4H). 19F NMR (282 MHz, CDCl3): δ −126.58 (4F), −123.26 (4F), −122.15 (4F), −121.87 (4F), −111.71 (4F), −81.16 (6F).

1. customA 100 ml Schlenk flask equipped with a stir bar
2. customwas flame-dried
3. customThe flask was evacuated
4. additionback-filled with argon three times
5. additionAnhydrous dimethylsulfoxide (30 mL) was added via a syringe
6. additionUpon completion of addition
7. customthen removed
8. temperaturefrom heat
9. additionThe reaction mixture was poured into 100 mL H2O/100 mL diethyl ether
10. stirringstirred vigorously for 30 min
11. customSolid residues were removed by filtration
12. washthe organic layer was washed twice with dilute NH4OH solution, twice with water
13. dry with materialdried over MgSO4
14. customThe solvent was removed by evaporation under reduced pressure

ORD record

ord-5cb3aac9293a43b18cf2a908d88c4cba

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156938B2