Sodium Iodide → 4-Chloro-2-iodophenol

HRID 369418Notes

Reaction equation

HRID 369418 reaction equation
N[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].N([O-])=O.[Na+].[I-:14].[Na+]>Cl.O>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([OH:9])=[C:2]([I:14])[CH:7]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 72652-Amino-4-chlorophenolHCID 23668193Sodium Nitrite

Product 1

HCID 6202344-Chloro-2-iodophenolYield 100.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Amino-4-chlorophenol (50 g, 0.35 mol) was dissolved in 500 ml of 2.5 N hydrochloric acid, to which an aqueous solution of 25.25 g (0.37 mol) of sodium nitrite in 50 ml of water was gradually added dropwise with cooling at 0° C. After stirring for 30 minutes, the reaction mixture was confirmed to show "positive" in an iodostarch reaction and an aqueous solution of 70 g (0.42 mol) of sodium iodide in 100 ml of water was added slowly. The temperature of the reaction mixture was allowed to rise to room temperature, at which the reaction mixture was stirred overnight and then extracted with ethyl acetate. The ethyl acetate layer was concentrated, whereby 89.7 g of 4-chloro-2-iodophenol were obtained as a purple solid (yield: 99%).

Workup

  1. additionwas gradually added dropwise
  2. customin an iodostarch reaction
  3. customto rise to room temperature, at which
  4. stirringwas stirred overnight
  5. extractionextracted with ethyl acetate
  6. concentrationThe ethyl acetate layer was concentrated

Sources & evidence

ORD record
ord-4bf69cbb4e7b4b5085dc1a9ff6192c73
Source dataset
uspto-grants-2000_10
Patent number
US06136848

Reaction notes

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