Imidazole → 1,3-Dichloro-2-{2-[4-(iodomethyl)phenoxy]ethoxy}-5-methylbenzene

HRID 2194862Notes

Reaction equation

HRID 2194862 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:20]I.[Cl:22][C:23]1[CH:40]=[C:39]([CH3:41])[CH:38]=[C:37]([Cl:42])[C:24]=1[O:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35]O)=[CH:31][CH:30]=1.N1C=CN=C1>C(Cl)Cl>[Cl:22][C:23]1[CH:40]=[C:39]([CH3:41])[CH:38]=[C:37]([Cl:42])[C:24]=1[O:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][I:20])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 67447508{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}methanol

Product 1

HCID 584884431,3-Dichloro-2-{2-[4-(iodomethyl)phenoxy]ethoxy}-5-methylbenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triphenylphosphine (1.1 eq.) and iodine (1.1 eq.) in CH2Cl2 (0.12M) at room temperature was added over 2 h a solution of the alcohol from step 3 (1 eq.) and imidazole (1.1 eq.) in CH2Cl2 (0.12M). The final mixture was stirred 14 h at room temperature. To the resulting suspension was added silica gel and the mixture was evaporated in vacuo. The residue was laid over a pad of silica gel, elution with Hex/EtOAc 10% afforded, after evaporation, the title compound as a white solid.

Workup

  1. additionTo the resulting suspension was added silica gel
  2. customthe mixture was evaporated in vacuo
  3. washThe residue was laid over a pad of silica gel, elution with Hex/EtOAc 10%
  4. customafforded
  5. customafter evaporation

Sources & evidence

ORD record
ord-5ee25d8fb64c40aab4b8302a9d7d13de
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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