Reaction #339342

Reaction equation

4-Bromo-7-methoxybenzo[b]thiophene

pyridine hydrochloride

→

title compound

Yield 41.0%

4-Chlorobenzo[b]thiophen-7-ol

Yield 41.0%

Conditions

Workup

1. 1
   OtherThe mixture was partitioned between HCl (aq.) (20 mL) and EtOAc (20 mL)
2. 2
   WashThe aqueous phase was washed with additional EtOAc (3×20 mL)
3. 3
   Dryingthe organic phase was dried (Na2SO4)
4. 4
   Concentrationconcentrated in vacuo
5. 5
   OtherThe product was purified by chromatography on silica gel with EtOAc:heptane (1:10 to 1:5

Procedure

4-Bromo-7-methoxybenzo[b]thiophene (prepared as described in J. Chem. Soc. (Perkin Trans I), 1983, 2973-2977) (1.2 g, 4.96 mmol) and pyridine hydrochloride (1.95 g, 16.87 mmol) was heated at 210° C. in a microwave for 15 min. The mixture was partitioned between HCl (aq.) (20 mL) and EtOAc (20 mL). The aqueous phase was washed with additional EtOAc (3×20 mL) and the organic phase was dried (Na2SO4) and concentrated in vacuo. The product was purified by chromatography on silica gel with EtOAc:heptane (1:10 to 1:5, v/v) as eluent to give the title compound as a red oil (372 mg, 41%).

Source