Imidazole → 4-(2-iodoethyl)phenol

HRID 133777Notes

Reaction equation

HRID 133777 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[OH:27][C:28]1[CH:36]=[CH:35][C:31]([CH2:32][CH2:33]O)=[CH:30][CH:29]=1.I.N1C=CN=C1>O.ClCCl>[I:25][CH2:33][CH2:32][C:31]1[CH:35]=[CH:36][C:28]([OH:27])=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 795Imidazole2×HCID 807IodineHCID 11776TriphenylphosphineHCID 86760696HCID 86760696, compound

Product 1

HCID 2456964-(2-iodoethyl)phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (1.57 g, 0.006 mol) and imidazole (0.41 g, 0.006 mol) were added to dry dichloromethane (20 ml). When the imidazole was in solution iodine (1.52 g, 0.006 mol) was added. After precipitation of the imidazole hydroiodide (4-hydroxyphenethyl) alcohol (0.69 g, 0.005 mol) was added. The mixture was stirred at room temperature for 4 h. Then water was added and the mixture was extracted with dichloromethane. The extracts were washed with water, dried and concentrated in vacuo to give a raw product. Purification by flash chromatography (heptane/ethyl acetate as a gradient eluent 9:1-6:4) gave a pure product. 1H NMR (400 MHz, DMSO-d6): 2.99 (2H, t, 3J=7.6 Hz), 3.38 (2H, t, 3J=7.6 Hz), 6.68 (2H, d, 3J=8.5 Hz), 7.03 (2H, d, 3J=8.5 Hz), 9.24 (1H, s, —OH).

Workup

  1. additionwas added
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe extracts were washed with water
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ee50908e1a44115932157e000847182
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

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