Ammonia → 2-(4-Chlorophenyl)-1-(4-fluoro-2-hydroxy-phenyl)-ethanone

HRID 14505

반응식

HRID 14505 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](Cl)=[O:10])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[F:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1.N>ClCCCl.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][C:19]=2[OH:23])=[O:10])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 97433-FluorophenolHCID 906924-Chlorophenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 687025202-(4-Chlorophenyl)-1-(4-fluoro-2-hydroxy-phenyl)-ethanone

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of 4-chlorophenylacetyl chloride (27.6 g, 0.15 mol) in 1,2-dichloroethane (200 ml), cooled to 0° C. in an ice bath, under nitrogen is added slowly AlCl3 (21.8 g, 0.16 mol). The reaction mixture is stirred at 0° C. for 20 min. 3-fluorophenol (12.2 g, 0.11 mol) is added, and the reaction mixture is allowed to warm to room temperature, then heated at 90° C. for 16 h. The reaction mixture is cooled to room temperature, then poured cautiously into aqueous ammonia solution (500 ml) with vigourous stirring. The mixture is diluted with CH2Cl2 (250 ml) and filtered through Celite. The organic phase is separated, washed with water, brine and dried (MgSO4). The solvent is removed in vacuo, and the crude product is purified by flash chromatography on silica gel using iso-hexane:ethyl acetate (10:1 to 4:1) as the eluent to give the title compound.

후처리

  1. temperatureto warm to room temperature
  2. temperatureheated at 90° C. for 16 h
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationfiltered through Celite
  5. customThe organic phase is separated
  6. washwashed with water, brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent is removed in vacuo
  9. customthe crude product is purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-44e1dcc8469d4abfa6010145fe0f0cf5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732435B2

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