Pyridinium chloride → 6,7-Dichloro-1-benzothiophene-5-ol

HRID 485848

Reaction equation

HRID 485848 reaction equation
[Cl:1][C:2]1[C:3]([O:12]C)=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[Cl:11].Cl.N1C=CC=CC=1>>[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[Cl:11]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 132899966,7-Dichloro-5-methoxybenzo[b]thiophene

Product 1

HCID 132899976,7-Dichloro-1-benzothiophene-5-olYield 1%

Procedure

A mixture of 45 g of 6,7-dichloro-5-methoxybenzo[b]thiophene and 5 g of pyridine hydrochloride is stirred at 180° for 1 hour. The mixture is cooled, triturated with water and extracted thrice with ether. The ether solution is washed with water, dried and concentrated to give 0.42 g of 6,7-dichloro-5-hydroxybenzo[b]thiophene as a tan-colored solid. Recrystallization from acetone-hexane gives prisms, mp 97°-98°.

Workup

  1. temperatureThe mixture is cooled
  2. customtriturated with water
  3. extractionextracted thrice with ether
  4. washThe ether solution is washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f9418678bf734ce5a33bda51e25e1af3
Source dataset
uspto-grants-1985_08
Patent number
US04537976

Linked notes

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