Potassium Phosphate, Tribasic → 2',6'-Dimethyl-4'-[3-(methylthio)propoxy]-6-phenoxybiphenyl-3-carbaldehyde

HRID 416176

Reaction equation

HRID 416176 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:5]=[O:6].[CH3:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][CH2:26][CH2:27][S:28][CH3:29])[CH:21]=[C:20]([CH3:30])[C:19]=1B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.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]>[CH3:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][CH2:26][CH2:27][S:28][CH3:29])[CH:21]=[C:20]([CH3:30])[C:19]=1[C:2]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 59342549{2,6-Dimethyl-4-[3-(methylthio)propoxy]phenyl}boronic acidHCID 593425893-Bromo-4-phenoxybenzaldehyde

Product 1

HCID 593426072',6'-Dimethyl-4'-[3-(methylthio)propoxy]-6-phenoxybiphenyl-3-carbaldehydeYield 70%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

3-Bromo-4-phenoxybenzaldehyde (1.11 g, 4.00 mmol), {2,6-dimethyl-4-[3-(methylthio)propoxy]phenyl}boronic acid (1.02 g, 4.00 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.263 g, 0.640 mmol) and tripotassium phosphate (1.70 g, 8.00 mmol) were dissolved in a mixed solvent of toluene (20 mL) and water (4 mL). After argon substitution, tris(dibenzylideneacetone)dipalladium(0) (0.147 g, 0.160 mmol) was added. The reaction mixture was stirred at 100° C. for 18 hr under argon atmosphere. The reaction mixture was allowed to cool, and water was added. The mixture was diluted with ethyl acetate, and the insoluble substance was filtered off through celite. The organic layer of the filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80) to give the title compound (1.13 g, yield 70%) as a yellow oil.

Workup

  1. temperatureto cool
  2. filtrationthe insoluble substance was filtered off through celite
  3. washThe organic layer of the filtrate was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80)

Sources & evidence

ORD record
ord-11a30c3d374d4da5adc8562981f66efe
Source dataset
uspto-grants-2012_01
Patent number
US08088821B2

Linked notes

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