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 732254노트

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HRID 732254 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
155 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7e1257a69b0b4a37b6ecd6f7715b72ca
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585982B2

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