Potassium Carbonate → 1-(2',5',5-Trifluoro-1,1'-biphenyl-2-yl)ethanone

HRID 2181914Notes

Reaction equation

HRID 2181914 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].Br[C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:26](=[O:28])[CH3:27]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:26](=[O:28])[CH3:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734335(2,5-Difluorophenyl)boronic acidHCID 27363041-(2-Bromo-4-fluorophenyl)ethan-1-one

Product 1

HCID 224822741-(2',5',5-Trifluoro-1,1'-biphenyl-2-yl)ethanoneYield 27.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalyst

Procedure

The title compound was prepared from 2,5-difluorophenylboronic acid (2.0 g, 12.7 mmol), tetrabutylammonium bromide (3.71 g, 11.5 mmol), potassium carbonate (4.78 g, 34.6 mmol), 2′-bromo-4′-fluoroacetophenone (2.5 g, 11.5 mmol), and palladium acetate (259 mg, 1.15 mmol) according to the procedure and in the same manner as described in Example 105, step a. The product was purified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g), eluting with a gradient of 10%-30% methyl tert-butyl ether in hexane, to afford the desired compound (784 mg, 27%) as a clear yellow oil.

Workup

  1. customThe product was purified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g)
  2. washeluting with a gradient of 10%-30% methyl tert-butyl ether in hexane

Sources & evidence

ORD record
ord-2d0eb55734bf4c42a36d138b27b01c32
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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