Sodium Iodide → HCID 20090642, compound

HRID 275183Notes

Reaction equation

HRID 275183 reaction equation
[C:1]12([C:11]3[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][C:12]=3[O:19][CH3:20])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[I-:21].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]12([C:11]3[CH:18]=[CH:17][C:14]([CH2:15][I:21])=[CH:13][C:12]=3[O:19][CH3:20])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 20090597HCID 20090597, compound

Product 1

HCID 20090642HCID 20090642, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To all of the above benzyl chloride in acetone (30 mL) is added sodium iodide (1.70 g., 10.0 mmol, 2.90 equiv.) and potassium carbonate (0.450 g., 10.5 mmol, 3.04 equiv.). The mixture is allowed to stir for 18 hours at room temperature. The solvents are evaporated, and the residue extracted twice with EtOAc. The extracts are washed with water and then brine. The organic phase is dried (MgSO4), and concentrated to afford 4-[1-adamantyl]-3-methoxybenzyl iodide (18b) (1.10 g., 2.88 mmol, 84%): mp=143°-144° C.; 1H NMR (300 MHz, CDCl3) δ 7.25 (d, J=7 Hz, 1H, ArH), 6.95 (d, J=7 Hz, 1H, ArH), 6.85 (s, 1H, ArH), 4.46 (s, 2H, ArCH2I), 3.85 (s, 3H, OCH3), 2.07 (s, 9H, adamantyl), 1.77 (s, 6H, adamantyl) .

Workup

  1. customThe solvents are evaporated
  2. extractionthe residue extracted twice with EtOAc
  3. washThe extracts are washed with water
  4. dry with materialThe organic phase is dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c10dc38984b748b7aa8699187ade82c5
Source dataset
uspto-grants-1995_02
Patent number
US05391817

Reaction notes

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