Potassium Iodide → 5-Benzyloxy-2-isopropoxyiodobenzene

HRID 1420858Notes

Reaction equation

HRID 1420858 reaction equation
N([O-])=O.[Na+].[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([O:20][CH:21]([CH3:23])[CH3:22])=[C:17](N)[CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[I-:24].[K+]>O.S(=O)(=O)(O)O>[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([O:20][CH:21]([CH3:23])[CH3:22])=[C:17]([I:24])[CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 187826085-Benzyloxy-2-isopropoxybenzeneamineHCID 23668193Sodium Nitrite

Product 1

HCID 187826685-Benzyloxy-2-isopropoxyiodobenzeneYield 48.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Sodium nitrite (589 mg, 8.5 mmol) in water (2.5 mL) was added dropwise to a stirred, cooled (0° C.) suspension of 5-benzyloxy-2-isopropoxybenzeneamine (Description 109, 2.05 g, 8.4 mmol) in aqueous sulfuric acid (2M, 14 mL). The mixture was stirred at 0° C. for 30 min., then added dropwise to a stirred, cooled (0° C.) solution of potassium iodide (2.50 g, 15.1 mmol) in water (10 mL). The mixture was stirred at room temperature for 90 min., then water (50 mL) was added. The mixture was extracted with ethyl acetate (3×50 mL). The combined organic fractions were washed with aqueous sodium thiosulfate (10%, 2×50 mL), hydrochloric acid (2M, 2×50 mL), saturated aqueous sodium hydrogen carbonate (2×50 mL), and brine (50 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/CH2Cl2 (80:20), to give the title compound as a cream solid (1.49 g, 48%). 1H NMR (360 MHz, CDCl3) δ 7.42-7.30 (6H, m), 6.90 (1H, dd, J 9.0, 2.9 Hz), 6.77 (1H, d, J 9.0 Hz), 4.98 (2H, s), 4.41 (1H, hept, J 6.1 Hz), and 1.35 (6H, d, J 6.1 Hz).

Workup

  1. temperaturecooled
  2. additionadded dropwise to a stirred
  3. stirringThe mixture was stirred at room temperature for 90 min.
  4. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  5. washThe combined organic fractions were washed with aqueous sodium thiosulfate (10%, 2×50 mL), hydrochloric acid (2M, 2×50 mL), saturated aqueous sodium hydrogen carbonate (2×50 mL), and brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluting with hexane/CH2Cl2 (80:20)

Sources & evidence

ORD record
ord-a76fbd0d6a41471583c96667fc52033c
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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