4-Aminophenol → 4-(4-Trifluoromethyl-benzyloxy)-phenylamine

HRID 855991노트

반응식

HRID 855991 반응식
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.[F:9][C:10]([F:20])([F:19])[C:11]1[CH:18]=[CH:17][C:14]([CH2:15]O)=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[F:9][C:10]([F:19])([F:20])[C:11]1[CH:18]=[CH:17][C:14]([CH2:15][O:8][C:3]2[CH:4]=[CH:5][C:6]([NH2:7])=[CH:1][CH:2]=2)=[CH:13][CH:12]=1

참가 물질

7

반응물 4

HCID 4034-AminophenolHCID 11776TriphenylphosphineHCID 676844-(Trifluoromethyl)benzenemethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

생성물 1

HCID 221378894-(4-Trifluoromethyl-benzyloxy)-phenylamine수율 55.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of p-aminophenol (0.200 g, 1.83 mmol), 4-trifluoromethylbenzyl alcohol (025 ml, 1.83 mmol) and triphenylphosphine (0.529 g, 2.02 mmol) in 5 ml anhydrous tetrahydrofuran was added diethyl azodicarboxylate (0.318 ml, 2.02 mmol). The reaction mixture was stirred overnight at room temperature under nitrogen. It was then diluted with 70 ml ethyl acetate and the resulting solution was washed sequentially with 50 ml saturated aqueous sodium bicarbonate solution, 50 ml water and 50 ml brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The solid residue was purified by flash column chromatography (silica gel, 15 g), eluting with 8:2 hexane/ethyl acetate to yield the title compound as an off-white solid (0.272 g, 55% yield). MS: 284.1 (M+1)

후처리

  1. washthe resulting solution was washed sequentially with 50 ml saturated aqueous sodium bicarbonate solution, 50 ml water and 50 ml brine
  2. dry with materialdried (anhydrous sodium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customThe solid residue was purified by flash column chromatography (silica gel, 15 g)
  5. washeluting with 8:2 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-461a073b170248c18ecf6d154c8e8b49
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262318B2

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