Imidazole → 1-Ethoxy-2-(2-iodoethyl)benzene

HRID 870468

Reaction equation

HRID 870468 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11]O)[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:37]I>ClCCl>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][I:37])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 2512712-(2-Ethoxyphenyl)ethanol

Product 1

HCID 895575981-Ethoxy-2-(2-iodoethyl)benzeneYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 50-mL round-bottom flask was placed dichloromethane (20 mL) and 2-(2-ethoxyphenyl)ethan-1-ol (1.33 g, 8.00 mmol, 1.00 equiv). The solution was cooled to 0° C. in a water/ice bath. Then PPh3 (2.72 g, 10.37 mmol, 1.30 equiv), imidazole (707 mg, 10.40 mmol, 1.30 equiv) and I2 (2.44 g, 9.61 mmol, 1.20 equiv) were added. The resulting solution was stirred at room temperature overnight. The reaction was then quenched by the addition of 50 mL of NaHSO3 (aq.). The organic layer was separated and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0:100). Purification afforded 1.34 g (61%) of 1-ethoxy-2-(2-iodoethyl)benzene as a colorless oil.

Workup

  1. customInto a 50-mL round-bottom flask was placed
  2. customThe reaction was then quenched by the addition of 50 mL of NaHSO3 (aq.)
  3. customThe organic layer was separated
  4. concentrationconcentrated under vacuum
  5. customPurification

Sources & evidence

ORD record
ord-195563b2318b40aeb23418b499615596
Source dataset
uspto-grants-2015_03
Patent number
US08969557B2

Linked notes

Loading…