Sodium Carbonate → 6-Cyclopropyl-2,2',4'-trifluoro-3-isopropoxybiphenyl-4-carbaldehyde

HRID 2272502Notes

Reaction equation

HRID 2272502 reaction equation
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.Br[C:43]1[C:48]([C:49]2[CH:54]=[CH:53][C:52]([F:55])=[CH:51][C:50]=2[F:56])=[C:47]([F:57])[C:46]([O:58][CH:59]([CH3:61])[CH3:60])=[C:45]([CH:62]=[O:63])[CH:44]=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[CH:1]1([C:43]2[C:48]([C:49]3[CH:54]=[CH:53][C:52]([F:55])=[CH:51][C:50]=3[F:56])=[C:47]([F:57])[C:46]([O:58][CH:59]([CH3:61])[CH3:60])=[C:45]([CH:62]=[O:63])[CH:44]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 1180381136-Bromo-2,2',4'-trifluoro-3-isopropoxybiphenyl-4-carbaldehyde

Product 1

HCID 1180380116-Cyclopropyl-2,2',4'-trifluoro-3-isopropoxybiphenyl-4-carbaldehydeYield 96%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Cyclopropylboronic acid (424 mg), a 2 M aqueous sodium carbonate solution (3.29 mL), tris(dibenzylideneacetone)dipalladium(0) (151 mg), and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (135 mg) were added at room temperature to a toluene (15 mL) solution of 6-bromo-3-isopropoxy-2,2′,4′-trifluorobiphenyl-4-carbaldehyde (615 mg), and the mixture was stirred at 100 C for 16 hours in an argon atmosphere. Water was added to the reaction mixture, and then, the mixture was filtered through celite. The filtrate was subjected to extraction with ethyl acetate. The organic layer was separated, then 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 (529 mg).

Workup

  1. filtrationthe mixture was filtered through celite
  2. extractionThe 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-8eb486a15d9b431a9f4fdab4240bd751
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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