Water → HCID 57678408, compound

HRID 491498Notes

Reaction equation

HRID 491498 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[OH:9].Br[CH2:11][C:12]#[N:13].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[I:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[O:9][CH2:11][C:12]#[N:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 183698972,5-Diiodophenol

Product 1

HCID 57678408HCID 57678408, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,5-diiodo-phenol (3.9 g, 11.28 mmol), bromoacetonitrile (2.03 g, 16.91 mmol) and potassium carbonate (3.11 g, 22.55 mmol) in 7 mL acetonitrile was sealed in a stoppered flask and stirred at room temperature for 18 hours. The reaction mixture was poured into water and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chomatographed on silica gel (30%-70% CH2Cl2/hexanes) to give 2.78 g of (2,5-Diiodo-phenoxy)-acetonitrile.

Workup

  1. customwas sealed in a stoppered flask
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10f40b90cd514041b8d354082758baf8
Source dataset
uspto-grants-2009_05
Patent number
US07531547B2

Reaction notes

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