Sodium Chloride → 6,7-Dichloro-5-hydroxy-2-hydroxymethylbenzo[b]thiophene

HRID 370985Notes

Reaction equation

HRID 370985 reaction equation
[Cl:1][C:2]1[C:3]([OH:14])=[CH:4][C:5]2[CH:9]=[C:8]([CH:10]=[O:11])[S:7][C:6]=2[C:12]=1[Cl:13].[BH4-].[Na+].[Cl-].[Na+]>C(O)C>[Cl:1][C:2]1[C:3]([OH:14])=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][OH:11])[S:7][C:6]=2[C:12]=1[Cl:13]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 132900376,7-Dichloro-2-formyl-5-hydroxybenzo[b]thiophene

Product 1

HCID 132900386,7-Dichloro-5-hydroxy-2-hydroxymethylbenzo[b]thiopheneYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6.0 g of 6,7-dichloro-2-formyl-5-hydroxybenzo[b]thiophene and 300 ml of 90% ethanol is added portionwise 1.5 g of sodium borohydride. The reaction mixture is stirred at room temperature for 20 min. Saturated sodium chloride solution is added and the mixture is extracted three times with ethyl acetate:ether (1:1). The combined organic extracts are washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated to give 4.5 g of 6,7-dichloro-5-hydroxy-2-hydroxymethylbenzo[b]thiophene, mp 167°-169°.

Workup

  1. extractionthe mixture is extracted three times with ethyl acetate:ether (1:1)
  2. washThe combined organic extracts are washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-7ae0655743644d20852b4ca8f0ff42f5
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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