Hydrochloric Acid → 2-Chloro-1-(3,4-difluorophenyl)ethanone

HRID 589821

반응식

HRID 589821 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:13][CH2:14][C:15](Cl)=[O:16].Cl>C(OCC)(=O)C.O>[Cl:13][CH2:14][C:15]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([F:8])[CH:4]=1)=[O:16]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 97061,2-DifluorobenzeneHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 23923212-Chloro-1-(3,4-difluorophenyl)ethanone수율 70%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

1,2-Difluorobenzene (150 g) and aluminium chloride (156 g) were charged in a round bottom flask. The reaction mixture is heated to about 60° C. followed by slow addition of chloroacetyl chloride (105 mL) over a period of 1 hour at the same temperature. The reaction mixture was stirred for another 3 hours followed by cooling to about 10° C. The reaction mass was poured into precooled water (1500 mL) followed by addition of hydrochloric acid (36%, 225 mL) at the same temperature and stirring. To this mixture ethyl acetate (750 mL) was charged and layers were separated. The aqueous layer is extracted with ethyl acetate (750 mL). The organic layers were combined and washed with water (750 mL) followed by complete evaporation of organic layer under vacuum at 50-55° C. The residue obtained is cooled to 25-35° C. followed by purification with column chromatography using 0-5% ethyl acetate in petroleum ether to afford the title compound in about 70% yield having HPLC purity of 99.51%.

후처리

  1. temperatureby cooling to about 10° C
  2. stirringstirring
  3. customlayers were separated
  4. extractionThe aqueous layer is extracted with ethyl acetate (750 mL)
  5. washwashed with water (750 mL)
  6. customfollowed by complete evaporation of organic layer under vacuum at 50-55° C
  7. customThe residue obtained
  8. temperatureis cooled to 25-35° C.
  9. customfollowed by purification with column chromatography

출처 및 근거

ORD 기록
ord-7d4365a7957542038a842d9eff747f40
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233966B2

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