Fluorobenzene → Methyl 6-(4-fluorophenyl)-6-oxohexanoate

HRID 395585

반응식

HRID 395585 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[C:13](=[O:22])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]>ClCCl.O>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:13](=[O:22])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:8][CH:7]=1

참가 물질

6

반응물 3

HCID 10008FluorobenzeneHCID 520737Methyl 6-chloro-6-oxohexanoateHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 69905189Methyl 6-(4-fluorophenyl)-6-oxohexanoate

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

반응 조건

온도
-5 °C

실험 절차

A suspension of 2.59 g (19.4.10−3 mol) of aluminum chloride in 4 ml of dichloromethane is prepared. It is cooled to −5° C. and a mixture of 0.97 ml (10.3.10−3 mol) of fluorobenzene and 1.31 ml (8.4.10−3 mol) of methyl 6-chloro-6-oxohexanoate in 3 ml of dichloromethane is added gradually, the temperature being maintained between −4 and −7° C. The temperature is then allowed to rise to 20° C. and, after 15 hours, the mixture is hydrolyzed in acidified iced water. It is extracted with dichloromethane and the organic phase obtained is washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The 2 g of crude product recovered in this way are purified by chromatography on silica gel using a petroleum ether/ethyl acetate mixture (96/4) as the eluent to give 1.26 g of the expected product in the form of a white powder (yield=63%).

후처리

  1. customis prepared
  2. additionis added gradually
  3. temperaturethe temperature being maintained between −4 and −7° C
  4. extractionIt is extracted with dichloromethane
  5. customthe organic phase obtained
  6. washis washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe 2 g of crude product recovered in this way
  10. customare purified by chromatography on silica gel using a petroleum ether/ethyl acetate mixture (96/4) as the eluent

출처 및 근거

ORD 기록
ord-4a0976bcd5cf4adeb77cbdd025bb3b9f
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06605633B1

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