Iodine → 4-Hydroxy-3-iodobenzonitrile

HRID 710393Notes

Reaction equation

HRID 710393 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[I:10]I>[NH4+].[OH-].O>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[I:10]

Participants

5

Reactant 2

HCID 807IodineHCID 130194-Cyanophenol

Product 1

HCID 109558154-Hydroxy-3-iodobenzonitrileYield 80.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of 4-hydroxybenzonitrile (0.5 g; 4.18 mmol) in 25% NH4OH (22 ml) a solution of I2 (1.06 g; 4.18 mmol) and KI (3.41 g; 20.54 mmol) in H2O (5 ml) was added at once with stirring. The stirring was continued for 6 h, during which time the mixture turn from black into colourless. The precipitate formed was filtered off and filtrate was evaporated to dryness under reduced pressure. The residue was treated with H2O (3 ml). The precipitate formed was filtered off, washed with cold H2O (3×2 ml), and dried in vacuo to give the title compound (0.82 g; 80%), as colourless solid. 1H-NMR (CDCl3) 6.03 (s, 1H); 7.03 (d, 1H, J=8.5 Hz); 7.53 (dd, 1H, J=1.9 Hz, 8.5 Hz); 7.96 (d, 1H, 1.9 Hz).

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered off
  3. customfiltrate was evaporated to dryness under reduced pressure
  4. additionThe residue was treated with H2O (3 ml)
  5. customThe precipitate formed
  6. filtrationwas filtered off
  7. washwashed with cold H2O (3×2 ml)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-c6ba1da91ea34a769c056e95dee2f1ae
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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