Potassium Iodide → Methyl 3-hydroxy-4-iodobenzoate

HRID 408565Notes

Reaction equation

HRID 408565 reaction equation
N[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].N([O-])=O.[Na+].[I-:17].[K+]>C1COCC1.Cl.O>[OH:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[I:17])[C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 3

HCID 4875Potassium IodideHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 10378812Methyl 3-hydroxy-4-iodobenzoate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 4-amino-3-hydroxybenzoate (1 eq.) in THF was diluted with aqueous HCl 3N and cooled to 0° C. Sodium nitrite (1.1 eq.) in H2O was added over 5 min. The reaction mixture was stirred for 25 min at 0° C. and then a solution of potassium iodide (4 eq.) in H2O was added in one portion, and stirred for 15 min. The reaction mixture was partitioned between water and EtOAc, the organic layer was washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with DCM) to afford methyl 3-hydroxy-4-iodobenzoate.

Workup

  1. stirringstirred for 15 min
  2. customThe reaction mixture was partitioned between water and EtOAc
  3. washthe organic layer was washed with saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by chromatography on silica gel (elution with DCM)

Sources & evidence

ORD record
ord-c7ac09995dfd43c7bde04503831f5273
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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