Water → (5-Bromo-2-fluoro-4-methoxy-phenyl)-(3-fluoro-phenyl)-methanone

HRID 1610111Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9](Cl)=[O:10].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[O:23][CH3:24].O>ClCCl>[Br:15][C:16]1[C:17]([O:23][CH3:24])=[CH:18][C:19]([F:22])=[C:20]([C:9]([C:8]2[CH:12]=[CH:13][CH:14]=[C:6]([F:5])[CH:7]=2)=[O:10])[CH:21]=1

Participants

Conditions

Temperature: -60 °C

Procedure

A total of 716 mg of aluminium chloride was suspended in 24.4 ml of dichloromethane and was then mixed with 0.65 ml of 3-fluorobenzoyl chloride and 1 g of 1-bromo-4-fluoro-2-methoxy-benzene obtained in Production Example II-1-a under stirring at −60° C. The mixture was raised in temperature to room temperature over 2.5 hours and was stirred for further 3 hours. Water was added to the reaction mixture under ice-cooling, followed by extracting with diethyl ether. The resulting organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:10), to give 856 mg of the title compound as white crystals.

Workup

temperatureThe mixture was raised in temperature to room temperature over 2.5 hours
stirringwas stirred for further 3 hours
temperaturecooling
extractionby extracting with diethyl ether
washThe resulting organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine
dry with materialdried over magnesium sulfate
customthe solvent was evaporated
customThe residue was purified
customseparated by silica gel column chromatography (ethyl acetate:hexane=1:10)

Sources & evidence

ORD record: ord-43f23cd3818549a7a4f0d104a23ea711
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982274B2

Reaction notes

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