Triethylamine → Ethyl 2-(4-amino-3-iodophenyl)acetate

HRID 2301324Notes

Reaction equation

HRID 2301324 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)[CH3:2].C(N(CC)CC)C.[I:21]Cl>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([NH2:12])=[C:10]([I:21])[CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24640Iodine chlorideHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 18372435Ethyl 2-(4-amino-3-iodophenyl)acetateYield 48.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution (5° C.) of (4-aminophenyl)acetic acid ethyl ester (25 g, 0.39 mol) in CH2Cl2 (150 mL) is added triethylamine (14.1 g, 0.139 mmol) followed by a solution of iodine monochloride (21.5 g, 0.132 mol) in CH2Cl2 (100 mL). Cooling is removed and the reaction mixture is stirred for 4 hours at room temperature. The solution is concentrated in vacuo and chromatographed with a gradient of hexane/ethyl acetate (5%-30%) within 1 hour to give the desired product (19.5 g, 46%). MS: 305.9 (M+1)+.

Workup

  1. temperatureCooling
  2. customis removed
  3. concentrationThe solution is concentrated in vacuo
  4. customchromatographed with a gradient of hexane/ethyl acetate (5%-30%) within 1 hour

Sources & evidence

ORD record
ord-53495656cd1c4f3e8b0b4003ae4ebb6d
Source dataset
uspto-grants-2002_12
Patent number
US06500837B2

Reaction notes

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