Sulfuric Acid → (4-Fluoro-3-iodophenyl)methanol

HRID 1058677Notes

Reaction equation

HRID 1058677 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][OH:6].S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:20].[K+]>O>[F:10][C:9]1[CH:8]=[CH:7][C:4]([CH2:5][OH:6])=[CH:3][C:2]=1[I:20]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 13563644(3-Amino-4-fluorophenyl)methanolHCID 23668193Sodium Nitrite

Product 1

HCID 23497488(4-Fluoro-3-iodophenyl)methanolYield 50.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

The product from Example 8A (7.0 g, 50 mmol) in water (100 mL) at 0° C. was treated slowly with concentrated sulfuric acid (30 mL) at a rate to maintain the temperature below 10° C., then treated dropwise with an aqueous solution of sodium nitrite (3.45 g, 50 mmol). This solution was then added to a solution of potassium iodide (8.13 g, 50 mmol) in water (15 mL), heated to 60° C. for 2 hours, cooled, and extracted with methylene chloride. The organic phase was washed with 10% sodium hydroxide, 1 M sodium thiosulfate, 10% hydrochloric acid, aqueous sodium bicarbonate, dried (sodium sulfate), filtered, and the solvent evaporated. The crude product was purified by flash chromatography over silica gel (ethyl acetate/hexane 7:3) to provide 6.4 g of the title compound.

Workup

  1. temperatureto maintain the temperature below 10° C.
  2. temperaturecooled
  3. extractionextracted with methylene chloride
  4. washThe organic phase was washed with 10% sodium hydroxide, 1 M sodium thiosulfate, 10% hydrochloric acid, aqueous sodium bicarbonate
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe crude product was purified by flash chromatography over silica gel (ethyl acetate/hexane 7:3)

Sources & evidence

ORD record
ord-9ba30ac02ba149bcb63b3b8283b476c4
Source dataset
uspto-grants-2003_02
Patent number
US06518279B2

Reaction notes

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