Iodine → HCID 57428844, compound

HRID 507619Notes

Reaction equation

HRID 507619 reaction equation
II.[PH2](O)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:16]2[S:17][CH:18]=[CH:19][N:20]=2)(O)[CH3:14])=[CH:9][CH:8]=1.[OH-].[Na+]>C(O)(=O)C>[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([C:16]2[S:17][CH:18]=[CH:19][N:20]=2)[CH3:14])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14798Sodium HydroxideHCID 4124402Phosphinic AcidHCID 57428843HCID 57428843, compound

Product 1

HCID 57428844HCID 57428844, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of iodine (856 mg, 3.37 mmol), hypophosphorous acid (3.152 mL, 20.22 mmol) and acetic acid (40 mL) was heated to 60° C. until the reaction mixture became clear. 1-(4-fluorophenyl)-1-(thiazol-2-yl)ethanol (1.05 g, 5.07 mmol) was added to the solution and the reaction mixture was heated to 80° C. overnight. After cooling to rt, the reaction mixture was neutralized with concentrated sodium hydroxide and the crude product was extracted with chloroform, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography with 0-40% ethyl acetate in hexane to afford the title compound as an oily brown residue (351 mg, 50% yield). MS (M+H)+ 208.

Workup

  1. temperaturethe reaction mixture was heated to 80° C. overnight
  2. temperatureAfter cooling to rt
  3. extractionthe crude product was extracted with chloroform
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography with 0-40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-99a43512c9f24fa7854078f0ffafd8db
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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