Carbon Tetrachloride → 4-(4-Methoxyphenyl)-benzofuran-7-carbaldehyde

HRID 1372159Notes

Reaction equation

HRID 1372159 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]3[CH:15]=[CH:16][O:17][C:13]=3[C:12]([CH3:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(Cl)(Cl)(Cl)Cl.C1C(=O)N(Br)C(=[O:27])C1.OP([O-])([O-])=O.[K+].[K+]>CC(N=NC(C#N)(C)C)(C#N)C.CC#N>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:14]3[CH:15]=[CH:16][O:17][C:13]=3[C:12]([CH:18]=[O:27])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 24450Potassium Phosphate, DibasicHCID 67184N-bromobutanimideHCID 210717824-(4-Methoxyphenyl)-7-methylbenzofuran

Product 1

HCID 210717834-(4-Methoxyphenyl)-benzofuran-7-carbaldehydeYield 78.7%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 6342AcetonitrileSolvent

Procedure

To a 250 ml round bottom flask was added 4-(4-methoxyphenyl)-7-methylbenzofuran (600 mg, 2.52 mmol), CCl4 (70 ml), NBS (490 mg, 2.77 mmol), and a catalytic amount of AIBN (25 mg). The reaction was brought to reflux for 2 h after which the reaction was allowed to cool, the solids were filtered off, and the solution concentrated. CH3CN (30 ml), K2HPO4 (440 mg, 2.53 mmol), and potassium benzeneselenite (630 mg, 2.77 mmol) were added and the reaction was brought to reflux for 2 h after. The reaction was cooled, passed through a silica plug (washed with 30% EtOAc/hex.), and concentrated to 810 mg of an orange solid. Further purification by chromatography (100% CH2Cl2) afforded 500 mg (78%) of product as a tan colored solid: mp 104–105° C.; 1H NMR (500 MHz, DMSO-d6): δ 3.85 (3H, s), 7.14 (2H, d, J=8.8 Hz), 7.20 (1H, d, J=2.2 Hz), 7.56 (1H, d, J=8.0 Hz), 7.69 (2H, d, J=8.8 Hz), 7.91 (1H, d, J=7.7 Hz), 8.26 (1H, d, J=2.2 Hz), 10.36 (1H, s); HRMS (ESI+) m/z 253.08622 ([M+H]+).

Workup

  1. temperatureto reflux for 2 h after which the reaction
  2. temperatureto cool
  3. filtrationthe solids were filtered off
  4. concentrationthe solution concentrated
  5. temperatureto reflux for 2 h after
  6. temperatureThe reaction was cooled
  7. concentrationconcentrated to 810 mg of an orange solid
  8. customFurther purification by chromatography (100% CH2Cl2)

Sources & evidence

ORD record
ord-3887411548a448ff899ea3c9cd148000
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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