反应详情

温度

23 °C

To a solution of 2-Bromo-6-(trans-4-tert-butyl-cyclohexyloxy)-naphthalene (500 mg, 0.001 mol) in Methylene chloride (2 mL, 0.03 mol), N-iodosuccinimide (600 mg, 0.003 mol) was added, followed by zirconium tetrachloride (60 mg, 0.0003 mol) at 23° C. The reaction mixture was then sonicated and stirred for 5 minutes at 23° C. Reaction was then diluted with DCM and the solids were removed via filtration through a 4 micron filter. 1 g of SiO2 was added directly to the solution and the solvent was then removed under reduced pressure. The SiO2 was then loaded onto a column (SiO2, 24 g, 0-10% ethyl acetate/hexanes (ran neat hexanes for first 9 minutes of a 30 min gradient)) to give the DP as a tan amorphous solid with 20% impurity (SM) by HNMR. Material was then triturated with methanol, filtered, and dried on filter to give 386 mg of the desired product as a white solid in (60%). ESI-MS: 488 (M+H)+.

1. customThe reaction mixture was then sonicated
2. customReaction
3. customthe solids were removed via filtration through a 4 micron
4. filtrationfilter
5. addition1 g of SiO2 was added directly to the solution
6. customthe solvent was then removed under reduced pressure
7. customfor first 9 minutes
8. customof a 30 min
9. customto give the DP as a tan amorphous solid with 20% impurity (SM) by HNMR
10. customMaterial was then triturated with methanol
11. filtrationfiltered
12. customdried
13. filtrationon filter