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

HRID 69330

反応式

HRID 69330 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-8a63e1d89d654179884ad2e4fd5a9ac9
出典データセット
uspto-grants-2014_09
特許番号
US08822500B2

関連ノート

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