Potassium Carbonate → 4-Chlorobiphenyl

HRID 707209Notes

Reaction equation

HRID 707209 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-ChlorobiphenylYield 90%

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 plated mesh catalyst precursor (12 mm by 14 mm, wire diameter of 0.1 mm, opening of 0.154 mm) prepared in Example 6 and heated for 12 hours at 80° C. The reaction mixture was cooled to room temperature, and the mesh catalyst precursor was taken off from the mixture and washed with ethanol. 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 catalyst precursor taken off from the mixture could be recycled at least ten times with an average yield of not less than 90%. The wet-gilded type and the dry-gilded type provided the similar results.

Workup

  1. customprepared in Example 6
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed 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-738a9ab675ea4d5683e7d679c35508ba
Source dataset
uspto-grants-2015_11
Patent number
US09175004B2

Reaction notes

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