2-Nitropropane → 4-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)benzaldehyde

HRID 19769

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HRID 19769 반응식
[F:1][C:2]([F:17])([F:16])[C:3]([F:15])([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:4]([F:7])([F:6])[F:5].BrN1C(=[O:24])CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[N+](C(C)C)([O-])=O.[Na]>ClC(Cl)(Cl)Cl.C(O)C>[F:15][C:3]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[O:24])=[CH:10][CH:9]=1)([C:4]([F:7])([F:6])[F:5])[C:2]([F:16])([F:17])[F:1]

참가 물질

8

반응물 5

HCID 3982-NitropropaneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 1375814-(Heptafluoroisopropyl)tolueneHCID 5360545Sodium

생성물 1

HCID 860937714-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)benzaldehyde수율 30%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 5943Carbon Tetrachloride용매

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온도
0 °C

실험 절차

A solution of 3.5 g of 4-(heptafluoroisopropyl)-toluene (13.4 mmol) in 100 ml tetrachloromethane was heated to reflux. Then 2.63 g of N-bromosuccinimide (14.8 mmol) and 326 mg of dibenzoyl peroxide (1.34 mmol) were added in small portions. After 5 h the mixture was cooled to 0° C., filtered and the solvent was evaporated. The remaining residue was dissolved in 15 ml ethanol and was added to a suspension that had been prepared by addition of 2-nitropropane (1.4 ml, 15.5 mmol) to a solution of 340 mg sodium (14.8 mmol) in ethanol. This mixture was stirred for 3 days. Then it was filtered, the solvent was removed and the remaining residue was dissolved in EtOAc and washed with 1 N sodium hydroxide solution, 1 N HCl solution, saturated NaHCO3 solution and with brine. The EtOAc layer was then dried with magnesium sulfate, filtered and concentrated. Purification of the residue (silica gel; c-hexane/EtOAc 10:1) gave 1.1 g (30%) of 4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-benzaldehyde as a light yellow oil. 1H-NMR (CDCl3, 300 MHz: δ 7.82 (d, J=8 Hz, 2H), 8.03 (d, J=8 Hz, 2H), 10.11 (s, 1H).

후처리

  1. filtrationfiltered
  2. customthe solvent was evaporated
  3. dissolutionThe remaining residue was dissolved in 15 ml ethanol
  4. additionwas added to a suspension that
  5. filtrationThen it was filtered
  6. customthe solvent was removed
  7. dissolutionthe remaining residue was dissolved in EtOAc
  8. washwashed with 1 N sodium hydroxide solution, 1 N HCl solution, saturated NaHCO3 solution and with brine
  9. dry with materialThe EtOAc layer was then dried with magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification of the residue (silica gel; c-hexane/EtOAc 10:1)

출처 및 근거

ORD 기록
ord-e6d81247fd784eafbacc72fb4e7e2380
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745477B2

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