N-Iodosuccinimide → HCID 178445720, compound

HRID 713864Notes

Reaction equation

HRID 713864 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 92.6%

Reagents, catalysts & solvents 2

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

Procedure

A solution of 2-bromo-6-(trans-4-tert-butylcyclohexyloxy)naphthalene (160.0 g, 444.4 mmol) in methylene chloride (2.5 L) was purged under an atmosphere of argon. N-iodosuccinimide (202.1 g, 888.8 mmol) and zirconium tetrachloride (20.4 g, 88.9 mmol) was added and the reaction was stirred at room temperature under an atmosphere of argon. The reaction was monitored by 1H NMR and showed complete conversion to product after 30 minutes. The mixture was then concentrated under reduced pressure to give ˜250 g crude as a brown solid. The crude material was purified by silica gel chromatography with hexanes to give 200 g of desired product as a brown solid (yield: 92.6%). EDI-MS: 487.1 (M+H)+.

Workup

  1. customafter 30 minutes
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customto give ˜250 g crude as a brown solid
  4. customThe crude material was purified by silica gel chromatography with hexanes

Sources & evidence

ORD record
ord-7f7d228d6fc14913910f4a9aa3493667
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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