Imidazole → 1-Bromo-4-(2-iodoethoxy)benzene

HRID 605571Notes

Reaction equation

HRID 605571 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8]O)=[CH:4][CH:3]=1.N1C=CN=C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[I:36]I>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][I:36])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 991682-(p-Bromophenoxy)ethanol

Product 1

HCID 597566941-Bromo-4-(2-iodoethoxy)benzeneYield 67.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a sol. of compound 4 (39.2 g, 181 mmol) in dry toluene (500 mL) was added imidazole (61.5 g, 903 mmol), PPh3 (90 g, 343 mmol), and iodine (87.1 g, 343 mmol). This mixture was stirred at 60° C. for 2 h. The mixture was filtered over Celite, and the filtrate was concentrated under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:5→1:4→1:3→1:2→1:1) yielded the title compound (39.9 g, 67%).

Workup

  1. filtrationThe mixture was filtered over Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customPurification of the residue by FC (EtOAc/heptane 1:5→1:4→1:3→1:2→1:1)

Sources & evidence

ORD record
ord-a4854053e7ed4f9f813d9516fc06ae49
Source dataset
uspto-grants-2011_03
Patent number
US07915259B2

Reaction notes

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