N-(4-Bromo-3-fluoro-2-methylphenyl)acetamide → N-(4-Cyano-3-fluoro-2-methylphenyl)acetamide

HRID 751147노트

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HRID 751147 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[C:3]=1[F:13].[C:14]([Cu])#[N:15]>CN(C=O)C>[C:14]([C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[C:3]=1[F:13])#[N:15]

참가 물질

4

반응물 2

HCID 67123438N-(4-Bromo-3-fluoro-2-methylphenyl)acetamideHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 68454968N-(4-Cyano-3-fluoro-2-methylphenyl)acetamide수율 88.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

To a solution of N-(4-bromo-3-fluoro-2-methylphenyl)acetamide (72B) (2.18 g, 8.86 mmol) in DMF (20 mL) was added CuCN (2.61 g, 29.1 mmol). The mixture was stirred at 150° C. for 12 h and was then poured into ice (50 g). After warming to rt, the product was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried and concentrated. The residue was purified via flash chromatography eluting with a solution of 5% methanol in 95% of EtOAc/hexane (1:1) to provide the title compound (1.51 g) as a white solid. LCMS: m/z 193 [M+H]+

후처리

  1. temperatureAfter warming to rt
  2. extractionthe product was extracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified via flash chromatography
  7. washeluting with a solution of 5% methanol in 95% of EtOAc/hexane (1:1)

출처 및 근거

ORD 기록
ord-8080fcf545a8485b8dbff7794af3c7b6
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405234B2

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