Dimethylformamide → 3-Fluoro-2-formyl-N,N-diisopropyl-5-trifluoromethyl-benzamide

HRID 225552노트

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HRID 225552 반응식
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:15]=[C:16]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:17]([N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=[O:18].CN([CH:36]=[O:37])C>CCCCCC.C(OCC)C>[F:13][C:14]1[C:15]([CH:36]=[O:37])=[C:16]([CH:26]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:28]=1)[C:17]([N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:21])[CH3:22])=[O:18]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 442031433-Fluoro-N,N-diisopropyl-5-trifluoromethyl-benzamideHCID 178418339Butyllithium

생성물 1

HCID 577536553-Fluoro-2-formyl-N,N-diisopropyl-5-trifluoromethyl-benzamide수율 90%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8058Hexane용매

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온도
-75 °C

실험 절차

A dried 200 ml round-bottomed flask containing 20 ml diethylether was cooled to −75° C. then 22.15 mmol diisopropylamine, 22.15 mmol 1.6M n-butyllithium in hexane, and a solution of 14.77 mmol 3-fluoro-N,N-diisopropyl-5-trifluoromethyl-benzamide in 20 ml diethylether were added sequentially. The mixture was stirred at −75° C. for 2 hours. 2.9 ml DMF was added dropwise. After the reaction was stirred for another hour, the mixture was warmed and stirred at room temperature for 30 minutes. The mixture was quenched with 100 ml 10% citric acid and extracted 3 times with ether. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a light yellow solid (90% yield). MS (m/e): 320.1 (M+H+, 100%)

후처리

  1. stirringAfter the reaction was stirred for another hour
  2. temperaturethe mixture was warmed
  3. stirringstirred at room temperature for 30 minutes
  4. customThe mixture was quenched with 100 ml 10% citric acid
  5. extractionextracted 3 times with ether
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-0f1db3a63b324462a5f48e0996c1747e
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557114B2

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