Hydrochloric Acid → HCID 20083937, compound

HRID 1609151Notes

Reaction equation

HRID 1609151 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=2[C:9]=1[C:10](=[O:20])[C:11]1[CH:16]=[C:15]([I:17])[C:14]([OH:18])=[C:13]([I:19])[CH:12]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][C:35]([O:37]CC)=[O:36].[OH-].[K+].Cl>O.C(#N)C>[CH2:1]([C:5]1[O:6][C:7]2[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=2[C:9]=1[C:10](=[O:20])[C:11]1[CH:12]=[C:13]([I:19])[C:14]([O:18][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[C:15]([I:17])[CH:16]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 74769L-3373HCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 20083937HCID 20083937, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

32.8 g (60 mmol) of 2-butyl-3-[3,5-diiodo-4-hydroxybenzoyl]benzofuran and 13.8 g (100 mmol) of anhydrous potassium carbonate are initially introduced into 200 ml of acetonitrile. 17.6 g (90 mmol) of ethyl 4-bromobutyrate are added dropwise at room temperature within the space of 30 minutes and the suspension is subsequently heated under reflux for 14 h. Once the reaction solution has been cooled down to room temperature, 200 ml of distilled water are added and the mixture is extracted 3 times with 100 ml of methyl tert-butyl ether. The combined organic extracts are dried and concentrated to dryness. The residue, which consists of 2-butyl-3-[3,5-diiodo-4-(3-ethoxycarbonyl-propyloxy)benzoyl]benzofuran, is introduced into 100 ml of isopropanol and a solution of 39.6 g (600 mmol) of 85% potassium hydroxide in 400 ml of distilled water is added. The suspension is heated at about 60° C. until a clear solution is formed. Once the solution has been cooled down to room temperature, 100 ml of 1N hydrochloric acid are added, and the mixture is adjusted to pH 3 with 32% hydrochloric acid while cooling, and then extracted 3 times with 200 ml of MTB ether on each occasion. The combined organic, dried, rotary-evaporated extracts are taken up in 50 ml of dichloromethane and left at 0° C. for several hours. The pale brown crystals which have precipitated out are stirred up with a further 50 ml of dichloromethane. After filtering with suction, washing and drying, 5.7 g (20%) of almost colourless crystals of 2-butyl-3-[3,5-diiodo-4-(3-carboxypropyloxy)-benzoyl]benzofuran are obtained which can, if desired, be further purified on a silica gel column (MTB ether/methanol=9:1).

Workup

  1. temperaturethe suspension is subsequently heated
  2. temperatureunder reflux for 14 h
  3. extractionthe mixture is extracted 3 times with 100 ml of methyl tert-butyl ether
  4. customThe combined organic extracts are dried
  5. concentrationconcentrated to dryness
  6. additionis introduced into 100 ml of isopropanol
  7. temperatureThe suspension is heated at about 60° C. until a clear solution
  8. customis formed
  9. temperatureOnce the solution has been cooled down to room temperature
  10. temperaturewhile cooling
  11. extractionextracted 3 times with 200 ml of MTB ether on each occasion
  12. customThe combined organic, dried
  13. customrotary-evaporated extracts
  14. waitleft at 0° C. for several hours
  15. customThe pale brown crystals which have precipitated out
  16. filtrationAfter filtering with suction
  17. washwashing
  18. customdrying

Sources & evidence

ORD record
ord-68c9fb85b72e482e9deaa5e698e4deb0
Source dataset
uspto-grants-1995_03
Patent number
US05399672

Reaction notes

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