Sodium Carbonate → 2'-(2,4,6-Trimethoxybenzylthio)biphenyl-3-ol

HRID 1987476Notes

Reaction equation

HRID 1987476 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[C:4]=1[CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1B(O)O.I[C:25]1[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>[Pd].C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[C:4]=1[CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 122723-IodophenolHCID 686436172-(2,4,6-Trimethoxybenzylthio)phenylboronic acid

Product 1

HCID 668706052'-(2,4,6-Trimethoxybenzylthio)biphenyl-3-olYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 1.05 g 2-(2,4,6-trimethoxybenzylthio)phenylboronic acid (3.14 mmol), 1.07 g 3-iodophenol (4.9 mmol) and 0.195 g Pd catalyst was added 40 ml toluene followed by 15 ml 2M Na2CO3. The mixture was refluxed under nitrogen overnight. The mixture was extracted with ethyl acetate. The organic was washed with water, brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica flash chromatography (hexane:ethyl acetate 80:20) to afford 0.948 g product (2.48 mmol, 79% yield).

Workup

  1. temperatureThe mixture was refluxed under nitrogen overnight
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica flash chromatography (hexane:ethyl acetate 80:20)

Sources & evidence

ORD record
ord-64398d0dc5114e009aa6aabb0854497d
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Reaction notes

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