Hydrochloric Acid → 4-Fluoro-2-iodophenol

HRID 1420855Notes

Reaction equation

HRID 1420855 reaction equation
CC1C=CC(S([N-]Cl)(=O)=O)=CC=1.O.O.O.[Na+].[F:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.[I-:25].[Na+].Cl>CN(C)C=O.O>[F:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([I:25])[CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 97324-FluorophenolHCID 517414chloramine-T trihydrate

Product 1

HCID 101714174-Fluoro-2-iodophenolYield 18.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Chloramine-T trihydrate (50 g, 178 mmol) was added to a stirred, cooled (0° C.) solution of 4-fluorophenol (20 g, 178 mmol) and sodium iodide (26.7 g, 178 mmol) in dimethylformamide (250 mL). The mixture was stirred at 0° C. for 1 h., and poured into water (1000 mL). The mixture was acidified with hydrochloric acid (1M) and extracted with ether (4×200 mL). The combined organic fractions were washed with aqueous sodium thiosulfate (5%, 3×100 mL), water (2×50 mL) and brine (50 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The reside was purified by flash column chromatography on silica gel, eluting with hexane/CH2Cl2 to give the title compound as an off-white solid (7.8 g, 18%). 1H NMR (360 MHz, CDCl3) δ 5.08 (1H, s), 6.90-7.01 (2H, m), and 7.37 (1H, dd, J 7.6, 2.9 Hz).

Workup

  1. extractionextracted with ether (4×200 mL)
  2. washThe combined organic fractions were washed with aqueous sodium thiosulfate (5%, 3×100 mL), water (2×50 mL) and brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe reside was purified by flash column chromatography on silica gel
  6. washeluting with hexane/CH2Cl2

Sources & evidence

ORD record
ord-495e04ef4b0e454da603e3bf7469f98e
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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