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

HRID 1357739Notes

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

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, 1M 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. 1HNMR (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 organics washed with 10% sodium hydroxide, 1M sodium thiosulfate, 10% hydrochloric acid, aqueous sodium bicarbonate
dry with materialdried (sodium sulfate)
filtrationfiltered
customsolvent evaporated
customThe material was purified by flash chromatography over silica gel (ethyl acetate/hexane 7:3)

Sources & evidence

ORD record: ord-480fec26024d444fbf5ec6f7ee8a93ab
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06593335B1

Reaction notes

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