1-Nitro-2,5-bis(trifluoromethyl)benzene → 2,5-Bis(trifluoromethyl)aniline

HRID 868964

반응식

HRID 868964 반응식
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[C:14]([F:17])([F:16])[F:15])([O-])=O.Cl[Sn]Cl.O>CO.Cl>[F:15][C:14]([F:16])([F:17])[C:5]1[CH:6]=[CH:7][C:8]([C:10]([F:12])([F:13])[F:11])=[CH:9][C:4]=1[NH2:1]

참가 물질

5

반응물 2

HCID 27340481-Nitro-2,5-bis(trifluoromethyl)benzeneHCID 43835034Tin dichloride dihydrate

생성물 1

HCID 7198182,5-Bis(trifluoromethyl)aniline수율 85.9%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 887Methanol용매

반응 조건

온도
50 °C

실험 절차

To a solution of 2-nitro-1,4-bis(trifluoromethyl)benzene (3.3 g, 12.7 mmol) in methanol (15 mL) was added a solution of SnCl2.H2O (8.57 g, 38.1 mmol) in conc. HCl (15 mL) at room temperature, and the mixture was heated to 50° C. and stirred for 4 hours. Methanol was removed, and the aqueous solution was basified with conc. NaOH solution until pH 10. The suspension was diluted with EtOAc (100 mL), and the mixture was stirred at room temperature for 30 minutes and filtered. The solid was discarded, and the filtrate was washed with brine (50 mL), dried over sodium sulfate, and filtered. The solution was concentrated to give 2,5-bis(trifluoromethyl)benzenamine as a yellow oil (2.5 g). MS (ESI): m/z 230 [M+H]+.

후처리

  1. customMethanol was removed
  2. additionThe suspension was diluted with EtOAc (100 mL)
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. filtrationfiltered
  5. washthe filtrate was washed with brine (50 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe solution was concentrated

출처 및 근거

ORD 기록
ord-0a858d2e28904dfdb0f31798423e5cef
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969349B2

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