Potassium Carbonate → 4-Chlorobiphenyl

HRID 707208Notes

Reaction equation

HRID 707208 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 742994-Chlorophenylboronic acid

Product 1

HCID 163234-Chlorobiphenyl

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of iodobenzene (102 mg), 4-chlorophenylboronic acid (117 mg), and potassium carbonate (138 mg) in ethanol (3 ml) was added the mesh catalyst precursor (12 mm by 14 mm) prepared in Example 3 and heated for 12 hours at 80° C. The reaction mixture was cooled to room temperature, and the mesh catalyst precursor was washed with ethanol and taken off from the mixture. The solvent was distilled away from the reaction mixture under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane) to give an intended product, 4-chlorobiphenyl quantitatively. The mesh catalyst precursor taken off from the mixture was again used in the same reaction to again give the intended product, 4-chlorobiphenyl quantitatively. The mesh catalyst precursor could be recycled at least thirty times.

Workup

  1. customprepared in Example 3
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washthe mesh catalyst precursor was washed with ethanol
  4. distillationThe solvent was distilled away from the reaction mixture under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (n-hexane)

Sources & evidence

ORD record
ord-4d9aa523a6c74f02b1a4655c30ea52ba
Source dataset
uspto-grants-2015_11
Patent number
US09175004B2

Reaction notes

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