Potassium Carbonate → (3-Iodo-naphthalen-2-yloxy)-acetonitrile

HRID 502612Notes

Reaction equation

HRID 502612 reaction equation
[I:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Br[CH2:14][C:15]#[N:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(Cl)Cl>[I:1][C:2]1[C:3]([O:12][CH2:14][C:15]#[N:16])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 468320133-Iodonaphthalen-2-ol

Product 1

HCID 68461021(3-Iodo-naphthalen-2-yloxy)-acetonitrileYield 90.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-iodo-naphthalen-2-ol (2.0 g, 7.4 mmol), bromoacetonitrile (1.066 g, 8.88 mmol) and potassium carbonate (2.04 g, 14.81 mmol) in three mL of acetonitrile was stirred at room temperature for 16 hours. The reaction mixture was diluted with methylene chloride and filtered. The filtrate was washed with 2% aqueous NaOH solution, water, and saturated brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from EtOAc/hexanes to give 2.07 g of (3-iodo-naphthalen-2-yloxy)-acetonitrile, MP=105-107° C., MS (M+H)=309.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with 2% aqueous NaOH solution, water, and saturated brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-d0033861c8fb4ae58bf7c3bbf41b8396
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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