Hydrochloric Acid → 2-Chloro-5-iodophenol

HRID 1352855Notes

Reaction equation

HRID 1352855 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[O:9]C.B(Br)(Br)Br.C(=O)([O-])O.[Na+].Cl>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[OH:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 115870881-Chloro-4-iodo-2-methoxybenzene

Product 1

HCID 17144122-Chloro-5-iodophenolYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-chloro-4-iodo-2-methoxybenzene (1.34 g, 5 mmol) in dichloromethane was dropped under ice cooling a solution of 0.91M boron tribromide in dichloromethane (6.6 ml, 6.00 mmol) and the mixture was reacted for 1 hour under ice cooling and then for 3 days at room temperature. To the mixture was added an aqueous sodium hydrogencarbonate solution and then the mixture was acidified with concentrated hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed and purified with silica gel chromatography (hexane:ethyl acetate, 10:1) to give the subject compound (1.11 g, 87%) as white crystals.

Workup

  1. customthe mixture was reacted for 1 hour under ice cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed
  6. custompurified with silica gel chromatography (hexane:ethyl acetate, 10:1)

Sources & evidence

ORD record
ord-9bdd76a134a446a4b4dacd38fe41613b
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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