Pyridinium chloride → 4-Chlorobenzo[b]thiophen-7-ol

HRID 252160Notes

Reaction equation

HRID 252160 reaction equation
Br[C:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[C:5]([O:11]C)=[CH:4][CH:3]=1.[ClH:13].N1C=CC=CC=1>>[Cl:13][C:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[C:5]([OH:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 131232354-Bromo-7-methoxybenzo[b]thiophene

Product 1

HCID 574851324-Chlorobenzo[b]thiophen-7-olYield 41%

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%).

Workup

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

Sources & evidence

ORD record
ord-b8f76645aa9349108a2296cba2e371e8
Source dataset
uspto-grants-2011_01
Patent number
US07868017B2

Reaction notes

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