Imidazole → HCID 89557107, compound

HRID 870474Notes

Reaction equation

HRID 870474 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11]O)[CH2:2][CH3:3].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[I:32]I.N1C=CN=C1>ClCCl>[I:32][CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 21648789HCID 21648789, compound

Product 1

HCID 89557107HCID 89557107, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

Into a 50-mL round-bottom flask was placed 2-(2-propylphenyl)ethan-1-ol (240 mg, 1.46 mmol, 1.00 equiv), PPh3 (498 mg, 1.90 mmol, 1.30 equiv), I2 (446 mg), imidazole (129 mg) and dichloromethane (20 mL). The resulting solution was stirred for 16 h at 30° C. The reaction was then quenched by the addition of 100 mL of NaHSO3 (aq.). The resulting solution was extracted with 2×50 mL of dichloromethane and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100). Purification afforded 200 mg (50%) of 1-(2-iodoethyl)-2-propylbenzene 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 100 mL of NaHSO3 (aq.)
  3. extractionThe resulting solution was extracted with 2×50 mL of dichloromethane
  4. concentrationconcentrated under vacuum
  5. customPurification

Sources & evidence

ORD record
ord-e0af4ddd42d84a62b15a09c523e0dd67
Source dataset
uspto-grants-2015_03
Patent number
US08969557B2

Reaction notes

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