N-Iodosuccinimide → HCID 178445720, compound

HRID 1036448Notes

Reaction equation

HRID 1036448 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][C@H:13]3[CH2:18][CH2:17][C@H:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]3)[CH:8]=2)[CH:3]=1.[I:23]N1C(=O)CCC1=O>C(Cl)Cl.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([I:23])=[C:7]([O:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]1)[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 178445718HCID 178445718, compound

Product 1

HCID 178445720HCID 178445720, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-391ef005d9e242d5882e890f400ce38e
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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