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

HRID 561841ノート

反応式

HRID 561841 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3113e977140649649adde3ee3d4a5b46
出典データセット
uspto-grants-2011_11
特許番号
US08063105B2

反応ノート

読み込み中…