Methyl Ethyl Ketone → HCID 13985633, compound

HRID 370974Notes

Reaction equation

HRID 370974 reaction equation
[Cl:1][C:2]1[C:7]2[S:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:18].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].CC(=O)CC.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.CN(C)C=O>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][O:18][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])=[CH:9][S:8][C:7]=2[C:2]=1[Cl:1])[CH3:25]

Participants

7

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 13985632HCID 13985632, compound

Product 1

HCID 13985633HCID 13985633, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 8.3 g of 7chloro-6-hydroxy-3-(2-fluorophenyl)benzo[b]thiophene, 6.0 g of ethyl bromoacetate, 60 ml of 2-butanone, 5 ml of dimethylformamide and 4 g of potassium carbonate is heated under reflux until the standing material completely dissolves. Methylene chloride is added to the cooled reaction mixture and the resultant precipitate is collected. Evaporation of the filtrate gives 8.5 g of ethyl{[7-chloro-3-(2-fluorophenyl)benzo[b]thien-6-yl]oxy}acetate.

Workup

  1. temperatureis heated
  2. temperatureunder reflux until the standing material
  3. dissolutioncompletely dissolves
  4. customthe resultant precipitate is collected
  5. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-f2f896c22ec84f7d9ce9095d9cc391dd
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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