4-Bromo-5-methoxy-2-(4-methoxyphenyl)-benzofuran → 5-Methoxy-2-(4-methoxy-phenyl)benzofuran-4-carbonitrile

HRID 1794547Notes

Reaction equation

HRID 1794547 reaction equation
Br[C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[O:19][CH3:20].[Cu][C:22]#[N:23]>CN(C=O)C>[CH3:20][O:19][C:3]1[C:2]([C:22]#[N:23])=[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[O:10][C:6]2=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 102152694-Bromo-5-methoxy-2-(4-methoxyphenyl)-benzofuranHCID 178418546HCID 178418546, compound2×

Product 1

HCID 102861375-Methoxy-2-(4-methoxy-phenyl)benzofuran-4-carbonitrileYield 61.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-5-methoxy-2-(4-methoxyphenyl)-benzofuran 133 (0.258 g, 0.77 mmol) was taken into 20 mL of DMF along with copper (I) cyanide (0.173 g. 1.94 mmol) and heated at reflux for three hours. Additional copper (I) cyanide was added several times to complete the reaction. The reaction was filtered through a cotton plug that was then washed several times with ethyl acetate. The filtrate was diluted with additional ethyl acetate and then washed with water (2×), brine (1×), dried over magnesium sulfate, filtered and concentrated. The resulting material was purified by column chromatography on silica gel using 10% ethyl acetate in hexanes as the eluent to yield the desired compound (0.133 g, 61.8%) as a white solid: Mp. 120–122° C.; 1H NMR (DMSO-d6) δ 7.96 (d, 2 H, J=8.8 Hz), 7.92 (d, 1 H, J=9.1 Hz), 7.91 (s, 1 H), 7.14 (d, 1 H, J=9.1 Hz), 7.09 (d, 2 H, J=8.9 Hz), 3.95 (s, 3 H), 3.83 (s, 3 H); MS 280 (M +H)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for three hours
  3. customthe reaction
  4. filtrationThe reaction was filtered through a cotton plug that
  5. washwas then washed several times with ethyl acetate
  6. additionThe filtrate was diluted with additional ethyl acetate
  7. washwashed with water (2×), brine (1×)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting material was purified by column chromatography on silica gel using 10% ethyl acetate in hexanes as the eluent

Sources & evidence

ORD record
ord-101bbe65d8a04a1f8a3f6f9a517e8af4
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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