Sodium Carbonate → 2,2',3,4'-Tetrafluoro-[1,1'-biphenyl]-4-carbaldehyde

HRID 2272497Notes

Reaction equation

HRID 2272497 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.Br[C:48]1[CH:55]=[CH:54][C:51]([CH:52]=[O:53])=[C:50]([F:56])[C:49]=1[F:57]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[F:57][C:49]1[C:50]([F:56])=[C:51]([CH:52]=[O:53])[CH:54]=[CH:55][C:48]=1[C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27343342,4-Difluorophenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 269863904-Bromo-2,3-difluorobenzaldehyde

Product 1

HCID 1179922312,2',3,4'-Tetrafluoro-[1,1'-biphenyl]-4-carbaldehydeYield 94.9%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

(2,4-Difluorophenyl)boronic acid (5.39 g), a 2 M aqueous sodium carbonate solution (34.1 mL), tris(dibenzylideneacetone)dipalladium(0) (1.46 g), and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (1.40 g) were added at room temperature to a toluene (150 mL) solution of 4-bromo-2,3-difluorobenzaldehyde (5.03 g), and the mixture was stirred at 100 C for 16 hours in a nitrogen atmosphere. Water was added to the reaction mixture at room temperature, and the mixture was filtered through celite. Then, the filtrate was subjected to extraction with ethyl acetate. The organic layer was separated, washed with water and saturated saline in this order, and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (5.49 g).

Workup

  1. filtrationthe mixture was filtered through celite
  2. extractionThen, the filtrate was subjected to extraction with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and saturated saline in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c5a0a00a5c284a17890fbf4fec3658cd
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

Loading…