Hydrochloric Acid → 4-Chloro-3-iodophenol

HRID 1352860Notes

Reaction equation

HRID 1352860 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[I:10].C(=O)([O-])O.[Na+].Cl>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[I:10]

Participants

5

Procedure

To a solution of 1-chloro-2-iodo-4-methoxybenzene (2.68 g, 10.0 mmol) in dichloromethane (20 ml) was dropped under ice cooling 0.91M boron tribromide in dichloromethane (13.0 ml, 12.0 mmol). The mixture was stirred for 1 hour under ice cooling and for a day at room temperature. To the reaction mixture was added an aqueous saturated sodium hydrogencarbonate solution. The mixture was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution and dried over sodium sulfate. The solvent was removed to give the subject compound as pale brown crystals (2.61 g, quantitatively).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-04e55c6b9c5b41b5ac88bc802f496fc1
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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