Hydrochloric Acid → 3-Chloro-5-hydroxy-1-iodo-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]-benzene

HRID 497052Notes

Reaction equation

HRID 497052 reaction equation
C([O:9][C:10]1[CH:11]=[C:12]([Cl:32])[C:13]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=2)=[C:14]([I:16])[CH:15]=1)(=O)C1C=CC=CC=1.[OH-].[Na+].Cl>O1CCCC1.CO>[Cl:32][C:12]1[C:13]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][N:23]=2)=[C:14]([I:16])[CH:15]=[C:10]([OH:9])[CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 223186095-Benzoyloxy-3-chloro-1-iodo-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzene

Product 1

HCID 223186173-Chloro-5-hydroxy-1-iodo-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]-benzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.12 g of 5-benzoyloxy-3-chloro-1-iodo-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzene were dissolved in 16 ml of tetrahydrofuran and 7.8 ml of methanol, and 3.9 ml of 2N aqueous sodium hydroxide solution were added. After 30 minutes of stirring at room temperature. 3.9 ml of 2N hydrochloric acid were added, and the reaction mixture was concentrated under reduced pressure. Saturated sodium chloride solution and ethyl acetate were added to the residue, and the mixture was shaken. The ethyl acetate phase was isolated, dried and concentrated. The resulting crude product was purified chromatographically. Yield: 2.03 g (80%)

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionSaturated sodium chloride solution and ethyl acetate were added to the residue
  3. stirringthe mixture was shaken
  4. customThe ethyl acetate phase was isolated
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting crude product was purified chromatographically

Sources & evidence

ORD record
ord-0b1f00f0866c4f468d1216b30b5bd9f7
Source dataset
uspto-grants-2005_09
Patent number
US06949551B2

Reaction notes

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