Tributylphosphine → 2-[2-(4-Bromophenyl)ethoxy]-1,3-dichloro-5-methylbenzene

HRID 561843

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HRID 561843 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([Cl:19])[C:13]=1O.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>CCOCC.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:13]2[C:12]([Cl:11])=[CH:17][C:16]([CH3:18])=[CH:15][C:14]=2[Cl:19])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 13831TributylphosphineHCID 170772,6-Dichloro-4-methylphenolHCID 728512-(4-Bromophenyl)ethanolHCID 730421,1'-(Azodicarbonyl)dipiperidine

생성물 1

HCID 667612642-[2-(4-Bromophenyl)ethoxy]-1,3-dichloro-5-methylbenzene

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3283Diethyl Ether용매

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온도
80 °C

실험 절차

2-(4-Bromophenyl)ethanol (1 eq.) and 2,6-dichloro-4-methylphenol (1.5 eq.) were taken up in freshly deoxygenated toluene (0.1 M). To this solution was then added 1,1′-(azodicarbonyl)-dipiperidine (1.2 eq.) and finally tributylphosphine (1.2 eq.). The resulting yellow solution was heated at 80° C. for 2 h. The reaction mixture was cooled to RT, diluted with ether, and washed with 1 N aq. NaOH. The aqueous wash was back extracted with ether and the combined organic extracts were dried over MgSO4. Filtration and concentration of the filtrate in vacuo afforded a yellow semi-solid. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→10:1 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

후처리

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed with 1 N aq. NaOH
  3. washThe aqueous wash
  4. extractionwas back extracted with ether
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationFiltration and concentration of the filtrate in vacuo
  7. customafforded a yellow semi-solid
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, Hex→10:1 (v/v) Hex:EtOAc)

출처 및 근거

ORD 기록
ord-8f57794e0e284dbb9b873e52c33bd924
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063105B2

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