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

HRID 395585

Reaction equation

[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

Participants

Conditions

Temperature: -5 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-4a0976bcd5cf4adeb77cbdd025bb3b9f
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605633B1

Linked notes

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