Imidazole → 5-Chloro-3-(2-iodoethyl)-1-benzothiophene

HRID 1768018Notes

Reaction equation

HRID 1768018 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([CH2:10][CH2:11]O)[C:6]=2[CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:33]I.N1C=CN=C1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([CH2:10][CH2:11][I:33])[C:6]=2[CH:13]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 236144402-(5-Chloro-1-benzothiophene-3-yl)ethanol

Product 1

HCID 236144415-Chloro-3-(2-iodoethyl)-1-benzothiophene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(5-chloro-1-benzothiophene-3-yl)ethanol (1060 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-(5-chloro-1-benzothiophene-3-yl)ethyl iodide, was obtained as brown liquid; Yield: 1.1 g (69%); 319 (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-a859dc4280a94e7084171f97e5a7c750
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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