Sulfuric Acid → (4-Fluoro-3-iodophenyl)methanol
Reaction equation
N[C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[CH:6][C:7]=1[F:8].S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:20].[K+]>O>[F:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:9][OH:10])=[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 12A (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 at 60° C. for 2 hours, cooled and extracted with methylene chloride. The methylene chloride layer was washed with 10% sodium hydroxide, washed with 1 M 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. 1H NMR (300 MHz, CDCl3) δ 1.69 (t, 1H), 4.66 (d, 2H), 7.05 (t, 1H), 7.60 (d, 1H), 7.78 (dd, 1H).
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 1 M 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-ff7a560f68a645aaadb9974dde89c0ed
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06780872B2
Reaction notes
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