Ethyl bromoacetate → HCID 13289995, compound

HRID 370937Notes

Reaction equation

HRID 370937 reaction equation
[Cl:1][C:2]1[C:3]([OH:18])=[CH:4][C:5]2[C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:8][S:7][C:6]=2[C:16]=1[Cl:17].Br[CH2:20][C:21]([O:23]CC)=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:3]([O:18][CH2:20][C:21]([OH:23])=[O:22])=[CH:4][C:5]2[C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:8][S:7][C:6]=2[C:16]=1[Cl:17]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 13289994HCID 13289994, compound

Product 1

HCID 13289995HCID 13289995, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.7 g of 6,7-dichloro-5-hydroxy-3-phenylbenzo[b]thiophene, 1.6 g of ethyl bromoacetate, 1.3 g of potassium carbonate and 30 ml of dimethylforamide is stirred at 60°-70° for 30 min. The mixture is filtered to remove inorganic salts and the filtrate is concentrated in vacuo to an oily residue. To the residue is added 10 mil of 40% sodium hydroxide and 30 ml of water and the mixture was heated on a steam bath for 30 min. After acidification of the mixture to pH 2, the solid product was extracted into ether, washed and dried. Concentration in vacuo gives 2.6 g of [(6,7-dichloro-3-phenylbenzo[b]thien-5-yl)oxy]acetic acid as crystals which have mp 152°-154° after recrystallization from acetone-hexane.

Workup

  1. filtrationThe mixture is filtered
  2. customto remove inorganic salts
  3. concentrationthe filtrate is concentrated in vacuo to an oily residue
  4. additionTo the residue is added 10 mil of 40% sodium hydroxide and 30 ml of water
  5. temperaturethe mixture was heated on a steam bath for 30 min
  6. extractionAfter acidification of the mixture to pH 2, the solid product was extracted into ether
  7. washwashed
  8. customdried
  9. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-b8853873ea9a4bd598476e1fd616b896
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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