Ethyl bromoacetate → Ethyl[(6,7-dichlorobenzo[b]thien-5-yl)oxy]acetate

HRID 485849

Reaction equation

HRID 485849 reaction equation
[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].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:3]([O:12][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[Cl:11]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 132899976,7-Dichloro-1-benzothiophene-5-ol

Product 1

HCID 13289999Ethyl[(6,7-dichlorobenzo[b]thien-5-yl)oxy]acetateYield 63.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.6 g of 6,7-dichloro-5-hydroxybenzo[b]thiophene, 3.0 g of ethyl bromoacetate, 1.5 g of potassium carbonate and 40 ml of anhydrous dimethylformamide is stirred at 70°-80° for 16 hours. The cooled mixture is diluted with ice-water (200 g) and the solid collected by filtration. Recrystallization of the crude product from acetone-hexane gives 3.2 g of ethyl [(6,7-dichlorobenzo[b]thien-5-yl)oxy]acetate as yellowish needles, mp 92°-93°.

Workup

  1. filtrationthe solid collected by filtration
  2. customRecrystallization of the crude product from acetone-hexane

Sources & evidence

ORD record
ord-1930dce74430403d89f3c7b8d41e4795
Source dataset
uspto-grants-1985_08
Patent number
US04537976

Linked notes

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