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

HRID 1836051노트

반응식

HRID 1836051 반응식
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

참가 물질

4

반응물 2

HCID 102152694-Bromo-5-methoxy-2-(4-methoxyphenyl)-benzofuranHCID 178418546HCID 178418546, 화합물2회

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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, 1H, 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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-fa992aab969c44bfb9c61b3fce0a605e
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06774248B2

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