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

HRID 1372167Notes

Reaction equation

HRID 1372167 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[O:16][CH:15]=[CH:14][C:13]=3[CH:12]=[C:11]([CH3:18])[CH:10]=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:4]=[CH:5][C:6]([C:9]2[C:17]3[O:16][CH:15]=[CH:14][C:13]=3[CH:12]=[C:11]([CH:18]=[O:22])[CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 24450Potassium Phosphate, DibasicHCID 67184N-bromobutanimideHCID 21071796HCID 21071796, compound

Product 1

HCID 210717987-(4-Methoxyphenyl)-benzofuran-5-carbaldehydeYield 67%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 7-(4-methoxyphenyl)-5-methyl-benzofuran (4.66 g, 19.58 mmol) in carbon tetrachloride (560 ml) was added NBS (3.83 g, 21.54 mmol) and AIBN (75 mg). The solution was brought to reflux for 4 h, cooled to room temperature, reduced by half, and the solids were filtered off. The solution was then concentrated to a yellow solid and anhydrous CH3CN (230 ml) was added. Then potassium benzeneselenite (5.34 g, 23.5 mmol), and K2HPO4 (4.09 g, 23.48 mmol) were added and then reaction was refluxed for 1.5 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 3.3 g (67%) product as a light orange solid: mp 79–80° C.; 1H NMR (300 MHz, DMSO-d6): δ 3.85 (3H, s), 7.13 (2H, d, J=8.8 Hz), 7.23 (1H, d, J=2.2 Hz), 7.88 (2H, d, J=8.8 Hz), 8.02 (1H, d, J=1.4 Hz), 8.23 (2H, m), 10.13 (1H, s); MS (ESI) m/z 253 ([M+H]+).

Workup

  1. temperatureto reflux for 4 h
  2. filtrationthe solids were filtered off
  3. concentrationThe solution was then concentrated to a yellow solid and anhydrous CH3CN (230 ml)
  4. additionwas added
  5. customreaction
  6. temperaturewas refluxed for 1.5 h after which it
  7. temperatureto cool to room temperature
  8. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-2a911d1fd12f46c59ce83c2f141e3f4d
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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