Imidazole → 3-(2-Iodoethyl)-1-benzothiophene

HRID 1768013Notes

Reaction equation

HRID 1768013 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][CH2:11]O)=[CH:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:32]I.N1C=CN=C1>C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][CH2:11][I:32])=[CH:2]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 158522062-(Benzo[b]thiophen-3-yl)ethanol

Product 1

HCID 236144373-(2-Iodoethyl)-1-benzothiophene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(1-benzothiophene-3-yl)ethanol (890 mg, 5 mmol) in anhydrous THF (50 ml), triphenylphosphine (1.572 g, 6 mmol), iodine (1.518 g, 6 mmol) and imidazole (408 mg, 6 mmol) were added at room temperature. The reaction mixture was stirred at room temperature for 4 hrs and quenched with water. It was extracted with chloroform, washed well with 5% Na2S2O3 solution and the organic layer was dried over anhydrous MgSO4. It was filtered and concentrated. The residue was purified by silica-gel column chromatography by eluting it with 30% ethyl acetate:hexane. The product, namely 2-(1-benzothiophene-3-yl)ethyl iodide, was obtained as brown liquid. Yield: 1.2 g (85%); 285 (M+H).

Workup

  1. customquenched with water
  2. extractionIt was extracted with chloroform
  3. washwashed well with 5% Na2S2O3 solution
  4. dry with materialthe organic layer was dried over anhydrous MgSO4
  5. filtrationIt was filtered
  6. concentrationconcentrated
  7. customThe residue was purified by silica-gel column chromatography
  8. washby eluting it with 30% ethyl acetate

Sources & evidence

ORD record
ord-9b9fb70f09f442fd87a07663cd3825d1
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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