Isopropenyl acetate → 2-Fluoro-4-biphenylyl acetone

HRID 376193

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([F:14])[CH:3]=1.C([O:18][C:19]([CH3:21])=[CH2:20])(=O)C.[O-]CCCC.C([Sn+](CCCC)CCCC)CCC.[F-].[K+]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[F:14][C:4]1[CH:3]=[C:2]([CH2:20][C:19](=[O:18])[CH3:21])[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

150 g of 4-bromo-2-fluorobiphenyl, 89.6 g of isopropenyl acetate, 258 ml of tributyltin butoxide and 4.7 g of a palladium chloride-tri(o-phenyl)phosphine complex were added to 300 ml of toluene and the mixture was stirred under heating at 80° C. for 2 hours under a nitrogen atmosphere. The reaction solution was left to cool to room temperature. Then, 1 l of ethyl acetate and 500 ml of a saturated potassium fluoride aqueous solution were added thereto, and the mixture was vigorously stirred. Insoluble matters were separated by filtration, and then the organic layer was collected by separation. The obtained organic layer was post-treated by a conventional method. The product was treated with hexane to obtain 106 g (yield: 78%) of 1-(2-fluoro-4-biphenylyl)-2-propanone.

Workup

waitThe reaction solution was left
temperatureto cool to room temperature
stirringthe mixture was vigorously stirred
customInsoluble matters were separated by filtration
customthe organic layer was collected by separation
additionThe obtained organic layer was post-treated by a conventional method
additionThe product was treated with hexane

Sources & evidence

ORD record: ord-2d7fdc5a43cd4017bb701985fef699f4
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488149

Linked notes

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