Imidazole → Benzene, (5-iodopentyl)-

HRID 2368760Notes

Reaction equation

HRID 2368760 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:37]I>ClCCl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][I:37])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 615235-Phenyl-1-pentanol

Product 1

HCID 561241Benzene, (5-iodopentyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-phenyl-pentane-1-ol (1.0 gm, 6.089 mmol) in dichloromethane (20 ml), triphenyl phosphine (2.35 gm, 8.52 mmol), imidazole (0.58 gm, 8.52 mmol) and elemental iodine (2.16 gm, 8.52 mmol) was stirred at room temperature for 12 h and solvent was removed under reduced pressure. The crude mixture was taken up in ethyl acetate (30 ml), washed with water (20 ml) and then with brine (30 ml). The layers were separated, the organic layer was dried over anhydrous sodium sulfate and solvent was removed under reduced pressure. The crude product was purified on column chromatography using hexane as an eluent to yield an oily liquid, 750 mg. 1H NMR (CDCl3): δ 1.30-1.70 (m, 4H), 1.80 (m, 2H), 2.6 (t, 2H, J=7.2 Hz), 3.10 (t, 2H, J=7.8 Hz), 7.00-7.34 (m, 5H).

Workup

  1. customsolvent was removed under reduced pressure
  2. washwashed with water (20 ml)
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate and solvent
  5. customwas removed under reduced pressure
  6. customThe crude product was purified on column chromatography
  7. customto yield an oily liquid, 750 mg

Sources & evidence

ORD record
ord-06dea5b425a14f62a216cfcaa7ad95ab
Source dataset
uspto-grants-2014_04
Patent number
US08703798B2

Reaction notes

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