Iodine → 2-(4-Amino-3-iodophenyl)ethanol

HRID 966520Notes

Reaction equation

HRID 966520 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Ca+2].[I:16]I>CO>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][C:3]=1[I:16]

Participants

5

Reactant 3

HCID 807IodineHCID 10112Calcium CarbonateHCID 669044-Aminophenethyl alcohol

Product 1

HCID 223118862-(4-Amino-3-iodophenyl)ethanolYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4-aminophenethyl alcohol (20 g, 145.8 mmol) and calcium carbonate (18.2 g, 145.8 mmol) in methanol (200 mL) was added iodine (37 g, 182.3 mmol) in portions. The mixture was heated at reflux overnight and then concentrated in vacuo to give a dark brown residue, which was partitioned between ethyl acetate and saturated sodium bisulfite solution. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give 14.1 g (37%) of desired product as a light brown syrup. MS(APCI+): m/z 264.1 (MH+). The compound was taken to Step B without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated in vacuo
  4. customto give a dark brown residue, which
  5. customwas partitioned between ethyl acetate and saturated sodium bisulfite solution
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-42ff094c58b34a68b1bc30d4982e5763
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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