Ethanol → 1,3-Bis(3-(2-pyridyl)phenyl)propan-2-ol

HRID 1160672Notes

Reaction equation

HRID 1160672 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([OH:18])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13](Br)[CH:12]=2)[CH:5]=[CH:6][CH:7]=1.C(OB([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[O-])(C(C)(C)C)C.C(=O)([O-])[O-].[Na+].[Na+].[CH2:40](O)[CH3:41]>C(OC(OCC)C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.O>[N:29]1[CH:41]=[CH:40][CH:32]=[CH:33][C:28]=1[C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([OH:18])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:28][N:29]=3)[CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 549190661,3-Bis(3-bromophenyl)propan-2-olHCID 131728382Pinacolyl-2-pyridylboronate

Product 1

HCID 595178931,3-Bis(3-(2-pyridyl)phenyl)propan-2-olYield 78.8%

Reagents, catalysts & solvents 4

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 7765AcetalSolvent

Procedure

1.64 g (5.4 mmol) of tri-o-tolylphosphine and subsequently 202 mg (0.9 mmol) of palladium(II) acetate were added to a vigorously stirred, degassed suspension of 33.3 g (90 mmol) of 1,3-bis(3-bromophenyl)propan-2-ol, 51.3 g (250 mmol) of pinacolyl-2-pyridylboronate and 40.3 g (380 mmol) of sodium carbonate in a mixture of 500 ml of diethoxyethane, 250 ml of ethanol and 350 ml of water. After the reaction mixture had been heated under reflux for 16 h, the aqueous phase was separated off, and the organic phase was washed with 500 ml of saturated sodium chloride solution and subsequently evaporated to dryness. The oily residue was recrystallised from toluene/acetonitrile, giving 26.0 g (71 mmol) of the product, having a purity of 98% according to 1H-NMR, corresponding to a yield of 78.8% of theory, in the form of colourless crystals.

Workup

  1. customdegassed
  2. temperatureAfter the reaction mixture had been heated
  3. temperatureunder reflux for 16 h
  4. customthe aqueous phase was separated off
  5. washthe organic phase was washed with 500 ml of saturated sodium chloride solution
  6. customsubsequently evaporated to dryness
  7. customThe oily residue was recrystallised from toluene/acetonitrile

Sources & evidence

ORD record
ord-99c4fff9afed426486bf5a1e92510f43
Source dataset
uspto-grants-2010_10
Patent number
US07816531B2

Reaction notes

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