Tributylphosphine → 2-(3-(4-Bromophenyl)propoxy)-3-chloro-1,4-difluorobenzene

HRID 561841노트

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HRID 561841 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[Cl:12][C:13]1[C:18]([F:19])=[CH:17][CH:16]=[C:15]([F:20])[C:14]=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:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][C:14]2[C:13]([Cl:12])=[C:18]([F:19])[CH:17]=[CH:16][C:15]=2[F:20])=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 27735612-Chloro-3,6-difluorophenolHCID 105606143-(4-Bromophenyl)propan-1-ol

생성물 1

HCID 667609722-(3-(4-Bromophenyl)propoxy)-3-chloro-1,4-difluorobenzene

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3283Diethyl Ether용매

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온도
80 °C

실험 절차

3-(4-Bromophenyl)propan-1-ol from the previous step (1 eq.) and 2-chloro-3,6-difluorophenol (1 eq.) were taken up in freshly deoxygenated toluene (0.3 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→15:1 (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→15:1 (v/v) Hex:EtOAc)

출처 및 근거

ORD 기록
ord-3113e977140649649adde3ee3d4a5b46
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063105B2

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