Sodium Iodide → Ethyl 1,4-benzodioxin-2-carboxylate

HRID 1756023Notes

Reaction equation

HRID 1756023 reaction equation
Br[C:2]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4][CH:3]1Br.[I-].[Na+]>CC(C)=O>[O:7]1[C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4][CH:3]=[C:2]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 11079061Ethyl 2,3-dibromo-1,4-benzodioxin-2-carboxylate

Product 1

HCID 10987416Ethyl 1,4-benzodioxin-2-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Stir for 3 hours, at room temperature and under a nitrogen atmosphere, a mixture of 16 g (43.7 mmol) of ethyl 2,3-dibromo-1,4-benzodioxin-2-carboxylate and 24 g (160 mmol) of sodium iodide in 80 cm3 of anhydrous acetone. The reaction mixture is then concentrated under reduced pressure, hydrolysed with 80 cm3 of water, and subsequently extracted with diethyl ether. After treatment with an aqueous sodium thiosulfate solution followed by drying over magnesium sulfate, the ethereal phase is concentrated to dryness under reduced pressure and the crude product is purified by chromatography on a silica column (eluant: petroleum ether/diethyl ether, 40:60). Ethyl 1,4-benzodioxin-2-carboxylate is thereby obtained in a yield of 85%. Melting point: 42° C. ##STR29##

Workup

  1. concentrationThe reaction mixture is then concentrated under reduced pressure, hydrolysed with 80 cm3 of water
  2. extractionsubsequently extracted with diethyl ether
  3. dry with materialby drying over magnesium sulfate
  4. concentrationthe ethereal phase is concentrated to dryness under reduced pressure
  5. customthe crude product is purified by chromatography on a silica column (eluant: petroleum ether/diethyl ether, 40:60)

Sources & evidence

ORD record
ord-54caf4d3333e4246931ee266e47e3f6c
Source dataset
uspto-grants-1995_08
Patent number
US05439909

Reaction notes

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