Ethyl bromoacetate → HCID 13290011, compound

HRID 652620Notes

Reaction equation

HRID 652620 reaction equation
[Cl:1][C:2]1[C:3]([OH:14])=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH3:11])[S:7][C:6]=2[C:12]=1[Cl:13].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:3]([O:14][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH3:11])[S:7][C:6]=2[C:12]=1[Cl:13]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 13290010HCID 13290010, compound

Product 1

HCID 13290011HCID 13290011, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.15 g of 6,7-dichloro-2-ethyl-5-hydroxybenzo[b]thiophene, 0.87 g of ethyl bromoacetate, 0.4 g of potassium carbonate and 12 ml of dimethylformamide is stirred at 90° for 20 min. The cooled mixture is diluted with 100 g of ice water and the solid collected by filtration. Recrystallization of the crude product from pentane gives 1.3 g of ethyl [(6,7-dichloro-2-ethylbenzo[b]thien-5-yl)oxy]acetate as colorless prisms, mp 67°-68°.

Workup

  1. filtrationthe solid collected by filtration
  2. customRecrystallization of the crude product from pentane

Sources & evidence

ORD record
ord-4cebdf986d2a405f99391d5d81531886
Source dataset
uspto-grants-1987_06
Patent number
US04672138

Reaction notes

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