2-(6-Bromo-3,4-diethoxy-2-fluorobenzyl)isoindol-1,3-dione → 2-(6-Cyano-3,4-diethoxy-2-fluorobenzyl)isoindol-1,3-dione

HRID 732254ノート

反応式

HRID 732254 の反応式
Br[C:2]1[C:7]([CH2:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])=[C:6]([F:20])[C:5]([O:21][CH2:22][CH3:23])=[C:4]([O:24][CH2:25][CH3:26])[CH:3]=1.[Cu](C#N)[C:28]#[N:29]>CN(C)C=O>[C:28]([C:2]1[C:7]([CH2:8][N:9]2[C:10](=[O:19])[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]2=[O:18])=[C:6]([F:20])[C:5]([O:21][CH2:22][CH3:23])=[C:4]([O:24][CH2:25][CH3:26])[CH:3]=1)#[N:29]

参加物

4

反応物 2

HCID 578383662-(6-Bromo-3,4-diethoxy-2-fluorobenzyl)isoindol-1,3-dioneHCID 178418260HCID 178418260、化合物

生成物 1

HCID 578383672-(6-Cyano-3,4-diethoxy-2-fluorobenzyl)isoindol-1,3-dione収率 60%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
155 °C

実験手順

A mixture of 2-(6-bromo-3,4-diethoxy-2-fluorobenzyl)isoindol-1,3-dione (1.00 g, 2.37 mol), copper cyanide (0.42 g, 4.74 mol) and N,N-dimethylformamide (5 mL) was stirred at 155° C. for ten hours. After the reaction mixture was extracted with a 10% aqueous solution of ethylene diamine and toluene, the resultant organic layer was washed sequentially with a 10% aqueous solution of ethylene diamine and saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off to give crude crystals, which were washed with ethyl acetate to give 0.52 g of the title compound (yield: 60%) as slightly green crystals.

後処理

  1. extractionAfter the reaction mixture was extracted with a 10% aqueous solution of ethylene diamine and toluene
  2. washthe resultant organic layer was washed sequentially with a 10% aqueous solution of ethylene diamine and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. distillationthe solvent was distilled off
  6. customto give crude crystals, which
  7. washwere washed with ethyl acetate

出典と根拠

ORDレコード
ord-7e1257a69b0b4a37b6ecd6f7715b72ca
出典データセット
uspto-grants-2009_09
特許番号
US07585982B2

反応ノート

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