Iodine → HCID 67513096, compound

HRID 1508554Notes

Reaction equation

HRID 1508554 reaction equation
I([O-])(=O)(=O)=O.[Na+].[I:7]I.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=1>S(=O)(=O)(O)O>[F:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:14][C:15]=1[I:7]

Participants

5

Reactant 3

HCID 807IodineHCID 22906572Methyl 3-(4-fluorophenyl)propanoateHCID 23667635Sodium periodate

Product 1

HCID 67513096HCID 67513096, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

Sodium metaperiodate (0.971 g, 4.54 mmol) was slowly added to a solution of iodine (3.43 g, 13.5 mmol) in sulfuric acid (86 ml). This was stirred at room temperature for 30 minutes. This dark brown iodinating solution was then slowly added to a solution of methyl 3-(4-fluorophenyl)propanoate (5.20 g, 28.5 mmol) in sulfuric acid (28.5 ml) (pre-cooled to 0° C.) taking care not to let the temperature rise above 30° C. This was stirred for 50 min. further, and then the reaction was quenched by pouring onto 100 mL of stirring ice water. This was extracted with ethyl acetate (2×100 mL) and the combined organic layers were washed with water (100 mL) and brine (100 mL). The organic layer was dried over sodium sulfate and purified via column chromatography on a Biotage 40M column eluting with hexanes (1 CV) followed by a gradient of 0-50% ethyl acetate in hexanes to provide the desired product as a clear colorless liquid. 1H NMR (CDCl3, 500 MHz) δ 7.58 (dd, J=5.8 Hz, 1.9 Hz, 1H), 7.13 (m, 1H), 6.96 (t, J=8.2 Hz, 1H), 3.67 (s, 3H), 2.88 (t, J=7.7 Hz, 2H), 2.61 (t, J=7.7 Hz, 2H).

Workup

  1. customrise above 30° C
  2. stirringThis was stirred for 50 min. further
  3. customthe reaction was quenched
  4. additionby pouring onto 100 mL of stirring ice water
  5. extractionThis was extracted with ethyl acetate (2×100 mL)
  6. washthe combined organic layers were washed with water (100 mL) and brine (100 mL)
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. custompurified via column chromatography on a Biotage 40M column
  9. washeluting with hexanes (1 CV)

Sources & evidence

ORD record
ord-eb10d18647624396b412425c57ae4de1
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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