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

HRID 1386052Notes

Reaction equation

HRID 1386052 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 89A (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, extracted with methylene chloride, the organics washed with 10% sodium hydroxide, 1 M sodium thiosulfate, 10% hydrochloric acid, aqueous sodium bicarbonate, dried (sodium sulfate), filtered and solvent evaporated. The material 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 organics washed with 10% sodium hydroxide, 1 M sodium thiosulfate, 10% hydrochloric acid, aqueous sodium bicarbonate
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. customsolvent evaporated
  8. customThe material was purified by flash chromatography over silica gel (ethyl acetate/hexane 7:3)

Sources & evidence

ORD record
ord-47f48d29a2b64e419492c5711b5e54e0
Source dataset
uspto-grants-2001_07
Patent number
US06265417B1

Reaction notes

Loading…