Potassium Phosphate, Dibasic → 5-(4-Methoxy-phenyl)-benzofuran-7-carbaldehyde

HRID 1372162Notes

Reaction equation

HRID 1372162 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH3:18])[C:12]3[O:16][CH:15]=[CH:14][C:13]=3[CH:17]=2)=[CH:5][CH:4]=1.C1C(=O)N(Br)C(=[O:22])C1.OP([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:18]=[O:22])[C:12]3[O:16][CH:15]=[CH:14][C:13]=3[CH:17]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 24450Potassium Phosphate, DibasicHCID 67184N-bromobutanimideHCID 210717895-(4-Methoxyphenyl)-7-methyl-benzofuran

Product 1

HCID 210717905-(4-Methoxy-phenyl)-benzofuran-7-carbaldehydeYield 50.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5-(4-methoxyphenyl)-7-methyl-benzofuran (1.60 g, 2.83 g 1:1 ratio with 4-methoxy-biphenyl 6.72 mmol) in carbon tetrachloride (190 ml) was added NBS (1.32 g, 7.40 mmol) and AIBN (50 mg). The solution was brought to reflux for 2 h, cooled to room temperature, and the solids were filtered off. The solution was then concentrated and anhydrous CH3CN (80 ml) was added. Then potassium benzeneselenite (2.14 g, 9.41 mmol), and K2HPO4 (1.17 g, 6.72 mmol) were added and then reaction was heated to reflux for 1 h after which it was allowed to cool to room temperature. The solution was then passed through a silica plug and concentrated under high vacuum. Chromatography (100% CH2Cl2) afforded 850 mg (50%) product as a white solid: mp 94–95° C.; 1H NMR (300 MHz, DMSO-d6): δ 3.82 (3H, s), 7.08 (2H, d, J=8.8 Hz), 7.14 (1H, d, J=2.2 Hz), 7.71 (2H, d, J=8.8 Hz), 8.10 (1H, d, J=1.9 Hz), 8.21 (1H, d, J=2.2 Hz), 8.25 (1H, d, J=1.9 Hz), 10.37 (1H, s); MS (ESI) m/z 253 ([M+H]+).

Workup

  1. temperatureto reflux for 2 h
  2. filtrationthe solids were filtered off
  3. concentrationThe solution was then concentrated
  4. additionanhydrous CH3CN (80 ml) was added
  5. customreaction
  6. temperaturewas heated
  7. temperatureto reflux for 1 h after which it
  8. temperatureto cool to room temperature
  9. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-af8f9388d9d640ec8835d587aa4c0212
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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