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

HRID 1794547ノート

反応式

HRID 1794547 の反応式
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

参加物

4

反応物 2

HCID 102152694-Bromo-5-methoxy-2-(4-methoxyphenyl)-benzofuranHCID 178418546HCID 178418546、化合物2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-101bbe65d8a04a1f8a3f6f9a517e8af4
出典データセット
uspto-grants-2006_04
特許番号
US07022733B2

反応ノート

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