Sodium Carbonate → HCID 18445418, compound

HRID 460296Notes

Reaction equation

HRID 460296 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.[I:13]Cl.[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([I:13])[C:5]2[O:9][CH2:8][C:7]([CH3:10])([CH3:11])[C:6]=2[CH:12]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 24640Iodine chlorideHCID 53235955-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuran

Product 1

HCID 18445418HCID 18445418, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

5-Bromo-3,3-dimethyl-2,3-dihydro-benzofuran (example 1f) (10 g, 44 mmol) was dissolved in glacial acetic acid (40 mL), iodine monochloride (10.86 g, 66.9 mmol) was added and the reaction mixture was heated at reflux for 72 hours then cooled to 0° C., and 1N NaOH was slowly added until pH=8 followed by Na2CO3 until the solution become colorless. The solution was extracted with ethyl acetate and the organic layer further washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (10% ethyl acetate in hexane) to give 8.7 g of 5-bromo-7-iodo-3,3-dimethyl-2,3-dihydro-benzofuran (56%). 1H NMR (300 MHz; CDCl3): 1.34 (s, 6H), 4.32 (s, 2H), 7.13 (d, J=2 Hz, 1H), 7.58 (d, J=2 Hz, 1H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 72 hours
  3. extractionThe solution was extracted with ethyl acetate
  4. washthe organic layer further washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e7eb121b5955459181293145c6d82cf2
Source dataset
uspto-grants-2007_03
Patent number
US07196108B2

Reaction notes

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