Imidazole → (3-Iodomethyl-phenoxy)-acetic acid methyl ester

HRID 9241Notes

Reaction equation

HRID 9241 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:25]I.[CH3:27][O:28][C:29](=[O:40])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38]O)[CH:33]=1>ClCCl>[CH3:27][O:28][C:29](=[O:40])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][I:25])[CH:33]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 21554300Acetic acid, 2-[3-(hydroxymethyl)phenoxy]-, methyl ester

Product 1

HCID 69595626(3-Iodomethyl-phenoxy)-acetic acid methyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dichloromethane (85 mL) was added to Ph3P (4.942 g, 18.8 mmol), imidazole (1.311 g, 19.3 mmol) and I2 (4.735 g, 18.7 mmol). The mixture was stirred for 5 min. and then a solution of 12-2 (2.937 g, 15.0 mmol) in 15 mL dichloromethane was added by cannula. The reaction was stirred for 3 h, silica gel was added and the mixture evaporated. The residue was purified by flash chromatography on silica gel (10%→20%→30% ethyl acetate/hexanes) to give 12-3 (4.246 g, 13.9 mmol, 93%).

Workup

  1. stirringThe reaction was stirred for 3 h
  2. additionsilica gel was added
  3. customthe mixture evaporated
  4. customThe residue was purified by flash chromatography on silica gel (10%→20%→30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-426359c53dc648d09a60e6e056d141f4
Source dataset
uspto-grants-2006_08
Patent number
US07091231B2

Reaction notes

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