Hydrochloric Acid → 1-(3-tert-Butyl-4-hydroxy-5-iodophenyl)ethanone

HRID 2223766Notes

Reaction equation

HRID 2223766 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[I-:15].[Na+].ClN1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>CN(C)C=O.O.C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[C:9]([I:15])[C:10]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 137241451-(3-Tert-butyl-4-hydroxyphenyl)ethanone

Product 1

HCID 861743701-(3-tert-Butyl-4-hydroxy-5-iodophenyl)ethanoneYield 96.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(3-tert-Butyl-4-hydroxyphenyl)ethanone (384 mg, 2 mmol) and sodium iodide (360 mg, 2.4 mmol) were dissolved in a mixed solution of N,N-dimethylformamide (3 mL) and water (1 mL), and this was cooled in an ice bath. While stirring, N-chlorosuccinimide (NCS) (320 mg, 2.4 mmol) was added portionwise over 10 minutes. After stirring for 50 minutes, 2% aqueous sodium thiosulfate (4 mL), 2 N hydrochloric acid (1 mL), and ethyl acetate (10 mL) were added, and the solution was separated. The organic layer was washed with a mixed solution of 2% aqueous sodium thiosulfate (5 mL) and saturated brine (1 mL), and then with saturated brine (5 mL). The organic layer was dried, and concentrated under reduced pressure (50° C.) to obtain 616 mg of the subject compound as a yellowish oily substance (yield: 96.8%, HPLC purity: 93.2%).

Workup

  1. temperaturethis was cooled in an ice bath
  2. stirringAfter stirring for 50 minutes
  3. customthe solution was separated
  4. washThe organic layer was washed with a mixed solution of 2% aqueous sodium thiosulfate (5 mL) and saturated brine (1 mL)
  5. customThe organic layer was dried
  6. concentrationconcentrated under reduced pressure (50° C.)

Sources & evidence

ORD record
ord-65dc1d2bb25a4475be67302f31916868
Source dataset
uspto-grants-2008_05
Patent number
US07375236B2

Reaction notes

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