Potassium Carbonate → HCID 54408356, compound

HRID 1509627Notes

Reaction equation

HRID 1509627 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19](I)[CH:18]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:16][C:17]1[CH:18]=[C:19]([C:13]2[CH:14]=[CH:15][C:10]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:11][CH:12]=2)[CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 122691-Chloro-3-iodobenzeneHCID 1512531,1'-Biphenyl-4-yl-boronic acid

Product 1

HCID 54408356HCID 54408356, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of [1,1′-biphenyl]-4-ylboronic acid (8.47 g, 42.8 mmol), 1-chloro-3-iodobenzene (10 g, 41.9 mmol), Pd(PPh3)4 (0.969 g, 0.839 mmol) and K2CO3 (17.4 g, 126 mmol) in toluene (270 ml) and water (90 ml) was refluxed under nitrogen for 4.5 h. After cooling to room temperature, the organic phase was separated and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with brine and water, dried over Na2SO4 and the solvent was evaporated. The residue was purified by column chromatography on silica gel with heptane/DCM (98/2, v/v) as eluent to yield 3-chloro-1,1′:4′,1″-terphenyl (9.3 g, 84%) as a white solid.

Workup

  1. customthe organic phase was separated
  2. extractionthe aqueous phase was extracted with EtOAc
  3. washThe combined organic extracts were washed with brine and water
  4. dry with materialdried over Na2SO4
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography on silica gel with heptane/DCM (98/2

Sources & evidence

ORD record
ord-fd63458107764e06bfbce7b11e55758b
Source dataset
uspto-grants-2015_12
Patent number
US09224958B2

Reaction notes

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