Dimethylformamide → 2-(4-Bromo-2-chlorophenyl)-2-methylpropanenitrile

HRID 1438305노트

반응식

HRID 1438305 반응식
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#N)=[C:6]([Cl:13])[CH:5]=1.[CH3:14]I.C[N:17]([CH:19]=O)C>C1COCC1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:14])([CH3:11])[C:19]#[N:17])=[C:6]([Cl:13])[CH:5]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58762522(4-Bromo-2-chlorophenyl)acetonitrile

생성물 1

HCID 587626012-(4-Bromo-2-chlorophenyl)-2-methylpropanenitrile수율 87%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

NaH (95%, 1.18 g, 49.35 mmol) was suspended in DMF (25 mL) and cooled to 0° C. 4-bromo-2-chloro-phenyl)-acetonitrile (2.27 g, 9.87 mmol) from step 3 above, was dissolved in THF (10 mL) and slowly added via cannula and the reaction mixture stirred 20 min. MeI (6.10 mL, 98 mmol) was added and the resulting mixture was stirred overnight at room temperature. Reaction was quenched with H2O (50 mL). Solvents were removed in vacuo and residue partitioned between EtOAc and 1N HCl (50 mL). The organic phase was dried over Na2SO4 and evaporated. The crude organic product was purified by flash column chromatography (5% EtOAc in hexanes) to give the product (2.23 g, 87%) as a clear oil. 1H NMR (400 MHz, CDCl3): δ 7.34 (d, J=8.4 Hz, 1H), 7.43 (dd, J=8.4, 2.0 Hz, 1H), 7.61 (d, J=1.8 Hz, 1H).

후처리

  1. additionslowly added via cannula
  2. stirringthe resulting mixture was stirred overnight at room temperature
  3. customReaction
  4. customwas quenched with H2O (50 mL)
  5. customSolvents were removed in vacuo and residue
  6. custompartitioned between EtOAc and 1N HCl (50 mL)
  7. dry with materialThe organic phase was dried over Na2SO4
  8. customevaporated
  9. customThe crude organic product was purified by flash column chromatography (5% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-e2d663cd5faf4abc8bdc42e71d799b59
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622605B2

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