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Dimethylformamide → t-Butyl 3-bromo-5-cyanobenzoate

HRID 269557
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HRID 269557 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13](I)[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH3:16][N:17](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:16]#[N:17])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]
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참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 574859731,1-Dimethylethyl 3-bromo-5-iodobenzoate

생성물 1

HCID 69312160t-Butyl 3-bromo-5-cyanobenzoate수율 73%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

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온도
80 °C

실험 절차

A mixture of t-butyl 3-bromo-5-iodobenzoate (1.91 g, 5 mmol), zinc cyanide (585 mg, 5 mmol), and tetrakis(triphenylphosphine)palladium(0) (300 mg, 5 mol %) in dimethylformamide (20 ml) was heated at 80° C. for 2 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (20 ml) and washed with water and brine. The organic phase was dried and evaporated. Chromatography with ethyl acetate/hexane (1:4) gave the title compound as a colourless oil (1.02 g, 73%).

후처리

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate (20 ml)
  3. washwashed with water and brine
  4. customThe organic phase was dried
  5. customevaporated

출처 및 근거

ORD 기록
ord-960a87ef155a4261a08c9961438ceb7a
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07446222B2

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