Chloride → 3-phenoxythiophene

HRID 1899703Notes

Reaction equation

HRID 1899703 reaction equation
[Cl-].[C:2]1([OH:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:10]1[CH:14]=[CH:13][S:12][CH:11]=1.[H-].[Na+]>N1C=CC=CC=1>[O:8]([C:10]1[CH:14]=[CH:13][S:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 996PhenolHCID 133833-BromothiopheneHCID 24758Sodium hydride

Product 1

HCID 70189473-phenoxythiopheneYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Couprous chloride (3.08 g, 31.1 mmol) and phenol (8.78 g, 93.3 mmol) were sequentially added to a solution of 3-bromothiophene (5.06 g, 31.1 mmol) in pyridine (150 ml). Sodium hydride (3.73 g, 93.3 mmol, 60% dispersion in mineral oil) was then slowly added. The reaction was heated at reflux for 20 hours under Argon. The pyridine was removed under reduced pressure. The residue was diluted with EtO (200 ml) and washed with 1N NaOH (3×100 ml), 1N HCl (2×150 ml) and 1N NaOH (150 ml). The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was chromatographed using hexanes to give 3-phenoxy-thiophene as a clear oil (4.0 g, 74% yield).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 20 hours under Argon
  3. customThe pyridine was removed under reduced pressure
  4. additionThe residue was diluted with EtO (200 ml)
  5. washwashed with 1N NaOH (3×100 ml), 1N HCl (2×150 ml) and 1N NaOH (150 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was chromatographed

Sources & evidence

ORD record
ord-971af095f16046c3a0a4de9df5f1dfec
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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