Imidazole → Methyl 3-[3-(iodomethyl)phenyl]propanoate

HRID 15007Notes

Reaction equation

HRID 15007 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[I:20]I.N1C=CN=C1.[CH3:27][O:28][C:29](=[O:40])[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38]O)[CH:33]=1>ClCCCl>[CH3:27][O:28][C:29](=[O:40])[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][I:20])[CH:33]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 59794668Methyl 3-[3-(hydroxymethyl)phenyl]propanoate

Product 1

HCID 59794677Methyl 3-[3-(iodomethyl)phenyl]propanoateYield 81%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A mixture of Ph3P (36 mg, 0.14 mmol), I2 (41 mg, 0.16 mmol) and imidazole (10.5 mg, 0.15 mmol) in 0.40 mL 1,2-dichloroethane was stirred for 15 min. and then a solution of 18 (20.5 mg, 0.11 mmol) in 0.1 mL 1,2-dichloroethane was added by cannula. The resulting mixture was stirred for 1 h and then was filtered through basic alumina, washing with ethyl acetate. The filtrate was evaporated and the residue was purified by flash chromatography on silica gel to give compound 19 (26 mg, 81%).

Workup

  1. stirringThe resulting mixture was stirred for 1 h
  2. filtrationwas filtered through basic alumina
  3. washwashing with ethyl acetate
  4. customThe filtrate was evaporated
  5. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-8454a3519b8643b0b2e99e7fc262de07
Source dataset
uspto-grants-2010_06
Patent number
US07732443B2

Reaction notes

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