3-(Methylthio)-1-propanol → 2-Bromo-1,3-dimethyl-5-[3-(methylthio)propoxy]benzene

HRID 1908905

반응식

HRID 1908905 반응식
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[CH3:11][S:12][CH2:13][CH2:14][CH2:15]O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:15][CH2:14][CH2:13][S:12][CH3:11])=[CH:4][C:3]=1[CH3:10]

참가 물질

7

반응물 4

HCID 104483-(Methylthio)-1-propanolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 819704-Bromo-3,5-dimethylphenol

생성물 1

HCID 593425752-Bromo-1,3-dimethyl-5-[3-(methylthio)propoxy]benzene수율 87%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8058Hexane용매

실험 절차

To a solution of 4-bromo-3,5-dimethylphenol (4.02 g, 20.0 mmol), 3-(methylthio)-1-propanol (2.12 g, 20.0 mmol) and tributylphosphine (7.97 mL, 32.0 mmol) in toluene (320 mL) was added 1,1′-(azodicarbonyl)dipiperidine (8.07 g, 32.0 mmol), and the mixture was stirred at room temperature for 18 hr under nitrogen atmosphere. Hexane (160 mL) was added to the reaction mixture, the insoluble substance was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75) to give the title compound (5.03 g, yield 87%) as a pale-yellow oil.

후처리

  1. filtrationthe insoluble substance was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75)

출처 및 근거

ORD 기록
ord-e340654a9ac04344b2995fe6418edb08
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598226B2

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