Sodium Carbonate → HCID 16122316, compound

HRID 467415

Reaction equation

HRID 467415 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:10]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:11](B(O)O)=[CH:12][CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>COC>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([C:24]2[C:19]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 169713-BromoanisoleHCID 4589187Biphenyl-2-boronic acid

Product 1

HCID 16122316HCID 16122316, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8254Dimethyl EtherSolvent

Procedure

Under an argon atmosphere, 18.7 g of 3-bromoanisole, 23.8 g of 2-biphenylboronic acid and 2.31 g of tetraxis(triphenylphosphine)palladium(0) were placed in a flask. 340 mL of dimethyl ether (DME) and 170 mL of a 2M aqueous sodium carbonate solution were added to this flask, and the resultant was refluxed with stirring while heating for 8 hours. After cooling to room temperature, an aqueous phase was removed. An organic phase was washed with water and saturated brine, and then dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The resulting residue was purified by means of silica gel column chromatography, whereby 23.4 g (yield: 90%) of intended 3-methoxy[1,1′:2′,1″]terphenyl was obtained.

Workup

  1. temperaturethe resultant was refluxed
  2. temperaturewhile heating for 8 hours
  3. customan aqueous phase was removed
  4. washAn organic phase was washed with water and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationAfter the magnesium sulfate was filtered out
  7. concentrationthe organic phase was concentrated
  8. customThe resulting residue was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-89b77e8de0a0479085a03dbb5cf7c495
Source dataset
uspto-grants-2014_01
Patent number
US08623520B2

Linked notes

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