Sodium Carbonate → 6-Cyclopropyl-3-ethoxy-2,4'-difluorobiphenyl-4-carbaldehyde

HRID 2272512Notes

Reaction equation

HRID 2272512 reaction equation
Br[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[C:6]([F:15])[C:5]([OH:16])=[C:4]([CH:17]=[O:18])[CH:3]=1.[CH:19]1(B(O)O)[CH2:21][CH2:20]1.C(=O)([O-])[O-].[Na+].[Na+].[CH:31]1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCC[CH2:32]1>C(OCC)(=O)C.O.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].C1(C)C=CC=CC=1>[CH:19]1([C:2]2[C:7]([C:8]3[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=3)=[C:6]([F:15])[C:5]([O:16][CH2:31][CH3:32])=[C:4]([CH:17]=[O:18])[CH:3]=2)[CH2:21][CH2:20]1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 904231046-Bromo-2,4'-difluoro-3-hydroxybiphenyl 4 carbaldehyde

Product 1

HCID 904235146-Cyclopropyl-3-ethoxy-2,4'-difluorobiphenyl-4-carbaldehydeYield 318.6%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-bromo-2,4′-difluoro-3-hydroxybiphenyl-4-carbaldehyde (2.60 g), cyclopropylboronic acid (1.43 g), tris(dibenzylideneacetone)dipalladium(0) (0.760 g), a 2 M aqueous sodium carbonate solution (12.5 mL), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.682 g), and toluene (70 mL) was stirred overnight at 100 C in a nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate and water and then filtered through celite. The organic layer was separated from the filtrate, 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 (1.60 g).

Workup

  1. filtrationfiltered through celite
  2. customThe organic layer was separated from the filtrate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9ac2b8fb463d41118f0de1fd898144d6
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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