Cesium carbonate → 2-Isobutyl-5-nitrobenzonitrile

HRID 341328

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HRID 341328 반응식
Br[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH2:13](B(O)O)[CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.O.C(OCC)C>[CH2:13]([C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5])[CH:14]([CH3:16])[CH3:15]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 2734395(2-Methylpropyl)boronic acidHCID 70954232-Bromo-5-nitrobenzonitrile

생성물 1

HCID 222280302-Isobutyl-5-nitrobenzonitrile수율 58.9%

시약·촉매·용매 3

HCID 962Water용매2회HCID 1140Toluene용매HCID 3283Diethyl Ether용매

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온도
100 °C

실험 절차

Under an argon gas atmosphere, 2-bromo-5-nitrobenzonitrile (2.0 g), isobutylboronic acid (988 mg), cesium carbonate (5.7 g), and PdCl2 (dppf)-CH2Cl2 (720 mg) were dissolved in toluene (25 ml) and water (1 ml). The mixture was stirred at 100° C. for 18 hours. After the mixture was cooled to room temperature, the mixture was diluted with diethyl ether and water followed by the step of extraction/separation. The organic layer was washed with 1 N-hydrochloric acid, 5 N-sodium hydroxide aqueous solution and saturated brine, and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resulting residue was purified on column chromatography (EtOAc:hexane=1:3) to obtain the title compound (1.06 g) as a pale yellow oily substance.

후처리

  1. temperatureAfter the mixture was cooled to room temperature
  2. customfollowed by the step of extraction/separation
  3. washThe organic layer was washed with 1 N-hydrochloric acid, 5 N-sodium hydroxide aqueous solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified on column chromatography (EtOAc:hexane=1:3)

출처 및 근거

ORD 기록
ord-2103f95a344443ddb9b588fb4cb385b3
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895753B2

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