Nitroethane → 1,2,4,5-Tetrafluoro-3-(2-nitroprop-1-enyl)benzene

HRID 920456

반응식

HRID 920456 반응식
[F:1][C:2]1[C:9]([F:10])=[CH:8][C:7]([F:11])=[C:6]([F:12])[C:3]=1[CH:4]=O.[N+:13]([CH2:16][CH3:17])([O-:15])=[O:14].C1(N)CCCCC1>C(O)(=O)C>[F:11][C:7]1[CH:8]=[C:9]([F:10])[C:2]([F:1])=[C:3]([CH:4]=[C:16]([N+:13]([O-:15])=[O:14])[CH3:17])[C:6]=1[F:12]

참가 물질

5

반응물 3

HCID 6587NitroethaneHCID 7965CyclohexylamineHCID 6013312,3,5,6-Tetrafluorobenzaldehyde

생성물 1

HCID 866632051,2,4,5-Tetrafluoro-3-(2-nitroprop-1-enyl)benzene수율 91.1%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
80 °C

실험 절차

A mixture of 2,3,5,6-tetrafluorobenzaldehyde (25.0 g, 0.14 mol), nitroethane (21.08 g, 0.28 mol), and cyclohexylamine (13.92 g, 0.14 mol) in 150 mL of acetic acid was heated at 80° C. for 5-6 h under an argon atmosphere. After the end of the reaction was established by TLC, the reaction mixture was cooled to room temperature (rt) and the solvent was removed under vacuum. The residue was diluted with water, extracted with ethyl acetate three times. The combined extracts were dried over anhydrous MgSO4, filtered, and concentrated under vacuum. Product was purified by a silica gel chromatography using ethyl acetate and hexanes (1:6 to 1:4) as eluent to afford 30.0 g (91%) of the designed compound as yellow solid. Mass (ESI, positive) m/z 258.0 [M+Na]+.

후처리

  1. temperaturethe reaction mixture was cooled to room temperature (rt)
  2. customthe solvent was removed under vacuum
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate three times
  5. dry with materialThe combined extracts were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customProduct was purified by a silica gel chromatography

출처 및 근거

ORD 기록
ord-c14df3aa857842d59c81a52809e59ef6
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273055B2

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