Iodine → Ethyl 4-amino-3-iodobenzoate

HRID 1872037Notes

Reaction equation

HRID 1872037 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].C(Cl)Cl.[I:21]I>O>[I:21][C:12]1[CH:11]=[C:5]([CH:4]=[CH:3][C:2]=1[NH2:1])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 807IodineHCID 2337BenzocaineHCID 6344DichloromethaneHCID 516892Sodium Bicarbonate

Product 1

HCID 459320Ethyl 4-amino-3-iodobenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Part A: Ethyl 4-aminobenzoate (5.0 gr, 30.27 mmol) and sodium bicarbonate (3.81 g, 45.40 mmol, 1.5 eq.) were added to a 50:50 mixture of methylene chloride and water. The mixture was chilled to 0 degree and I2 (11.53 g, 45.40 mmol, 1.5 eq.) was added slowly. The reaction mixture was allowed to come to room temperature and was stirred for 72 hours. The layers were then separated and the aqueous layer washed with methylene chloride. All organics were combined and dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting oil was chromatographed on silica using 30% ethyl acetate in hexanes as solvent to afford ethyl 3-iodo-4-aminobenzoate. C9H10NO2I MS 292 (M+H)+ 309 (M+NH4)+.

Workup

  1. temperatureThe mixture was chilled to 0 degree
  2. customto come to room temperature
  3. customThe layers were then separated
  4. washthe aqueous layer washed with methylene chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting oil was chromatographed on silica using 30% ethyl acetate in hexanes as solvent

Sources & evidence

ORD record
ord-785155151cc746f291c80c1c0d25936b
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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