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

HRID 395585

反応式

HRID 395585 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-5 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-4a0976bcd5cf4adeb77cbdd025bb3b9f
出典データセット
uspto-grants-2003_08
特許番号
US06605633B1

関連ノート

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