Sulfuric Acid → (4-Fluoro-3-iodophenyl)methanol
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
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
The product from Example 30A (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. and 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 methylene chloride layer was washed with 10% sodium hydroxide, washed with 1M sodium thiosulfate, washed with 10% hydrochloric acid, washed with aqueous sodium bicarbonate, dried (sodium sulfate), filtered, and concentrated. The residue was purified by flash chromatography over silica gel (ethyl acetate/hexane 7:3) to provide 6.4 g of the title compound.
Workup
- temperatureto maintain the temperature below 10° C.
- temperaturecooled
- extractionextracted with methylene chloride
- washThe methylene chloride layer was washed with 10% sodium hydroxide
- washwashed with 1M sodium thiosulfate
- washwashed with 10% hydrochloric acid
- washwashed with aqueous sodium bicarbonate
- dry with materialdried (sodium sulfate)
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography over silica gel (ethyl acetate/hexane 7:3)
Sources & evidence
- ORD record
- ord-fc2f1b35e69d40289770d2d62c562cb3
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642222B2
Reaction notes
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