Azobisisobutyronitrile → Methyl 4-hydroxybenzofuran-2-carboxylate

HRID 2221444Notes

Reaction equation

HRID 2221444 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[O:10][C:6]=2[CH2:5][CH2:4][CH2:3]1.BrN1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[OH:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 14494063127724-12-3

Product 1

HCID 14494065Methyl 4-hydroxybenzofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a suspension of methyl 4-oxo-4,5,6,7-tetrahydro-benzofuran-2-ylcarboxylate (5.60 g, 28.8 mmol) in CCl4 (200 ml) were added N-bromosuccinimide (5.18 g, 28.8 mmol) and 2,2′-azobisisobutyronitrile (0.483 g, 2.88 mmol). The reaction mixture was heated at reflux for 80 min and concentrated in vacuo. The residue was suspended in ethyl acetate (200 ml), washed with saturated sodium bicarbonate solution (2×50 ml), brine (50 ml), dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography over silica gel with ethyl acetate/hexane (1/10) to yield methyl 4-hydroxy-benzofuran-2-ylcarboxylate as a while solid (4.21 g, 21.9 mmol).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 80 min
  3. concentrationconcentrated in vacuo
  4. washwashed with saturated sodium bicarbonate solution (2×50 ml), brine (50 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography over silica gel with ethyl acetate/hexane (1/10)

Sources & evidence

ORD record
ord-be0ff0be9abb4b1b8bafa58ecc59b94c
Source dataset
uspto-grants-2008_05
Patent number
US07368572B2

Reaction notes

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