Acetonitrile → 3-(2,6-Dichlorophenyl)-3-oxopropiononitrile

HRID 598175

반응식

HRID 598175 반응식
C([Li])CCC.[C:6](#[N:8])[CH3:7].[Cl:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:11]=1[C:12](OC)=[O:13]>C1COCC1>[Cl:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:11]=1[C:12](=[O:13])[CH2:7][C:6]#[N:8]

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 599542Methyl 2,6-dichlorobenzoateHCID 178418339Butyllithium

생성물 1

HCID 30181403-(2,6-Dichlorophenyl)-3-oxopropiononitrile수율 103.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

n-Butyl lithium (20.1 mL, 32.2 mmol, 1.6M in hexanes) was added to THF (30 mL) and the solution was cooled to −78° C. Acetonitrile (1.7 mL, 32 mmol) was added dropwise and the reaction stirred at the temperature for 45 minutes. Methyl 2,6-dichlorobenzoate (1.00 g, 4.88 mmol) was dissolved in 2 mL THF and added to the reaction mixture. The reaction stirred at −78° C. for 0.5 hr. The solution was quenched with methanol and warmed to room temperature. The material was diluted with water and 1N HCl. The solution was then extracted with Ethyl acetate, dried, and concentrated to give 1.08 g of desired product at 85% purity. Material used as is in the next step.

후처리

  1. additionadded to the reaction mixture
  2. stirringThe reaction stirred at −78° C. for 0.5 hr
  3. customThe solution was quenched with methanol
  4. temperaturewarmed to room temperature
  5. additionThe material was diluted with water and 1N HCl
  6. extractionThe solution was then extracted with Ethyl acetate
  7. customdried
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-77175a3bf88e461f971e10ca09d4c908
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897607B2

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