Phenol → 3-phenoxythiophene

Cuprous 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 Et2O (200 ml) and washed with 1 N NaOH (3×100 ml), 1 N HCl (2×150 ml) and 1 N 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).

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 Et2O (200 ml)
5. washwashed with 1 N NaOH (3×100 ml), 1 N HCl (2×150 ml) and 1 N NaOH (150 ml)
6. dry with materialThe organic layer was dried (MgSO4)
7. filtrationfiltered
8. customthe solvent was evaporated
9. customThe residue was chromatographed

ORD record

ord-0f488641c9744748bc4188fe2dc8c601

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06331637B1