Tetrahydrofuran → 3,5-Difluoro-4'-propyl-1,1'-biphenyl

HRID 1406822Notes

Reaction equation

[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].C1COCC1.[F:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[C:27]([F:29])[CH:28]=1>CCCCCC>[F:22][C:23]1[CH:24]=[C:25]([C:7]2[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=2)[CH:26]=[C:27]([F:29])[CH:28]=1

Participants

Conditions

Temperature: 60 °C

Procedure

In a nitrogen atmosphere, a solution prepared by mixing 90.33 g of 4-propylbromobenzene, 2.62 g of tetrakis-triphenylphosphine palladium, 240 mL of an aqueous potassium carbonate solution (2 mol/L), and 450 mL of THF was heated to 60° C., and 71.65 g of 3,5-difluorophenylboronic acid was added to the solution over 30 minutes. The resultant mixture was stirred at 60° C. for 30 minutes and then allowed to cool. Then, hexane was added to the mixture to separate an organic layer, and the organic layer was washed with saturated brine and dried by adding sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to yield 104.92 g of 3,5-difluoro-1-(4-propylphenyl)benzene.

Workup

customIn a nitrogen atmosphere, a solution prepared
temperatureto cool
customto separate an organic layer
washthe organic layer was washed with saturated brine
customdried
additionby adding sodium sulfate
distillationThen, the solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-836541e00bdb46cc860a99569269ab0e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916718B2

Reaction notes

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