4'-Chloro-4-ethylbiphenyl-3-ylboronic acid → HCID 178476534, compound

HRID 1470845Notes

Reaction equation

HRID 1470845 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[C:5]([O-:8])(=[O:7])[CH3:6].[C:9]([O-:12])(=[O:11])[CH3:10].C([O-])(=O)C.[Pb+4:17].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH3:32])=[C:27](B(O)O)[CH:26]=2)=[CH:21][CH:20]=1>>[C:1]([O-:4])(=[O:3])[CH3:2].[C:5]([O-:8])(=[O:7])[CH3:6].[C:9]([O-:12])(=[O:11])[CH3:10].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH3:32])=[C:27]([Pb+3:17])[CH:26]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 594459274'-Chloro-4-ethylbiphenyl-3-ylboronic acidHCID 178418268HCID 178418268, compound

Product 1

HCID 178476534HCID 178476534, compoundYield 100%

Conditions

Temperature
40 °C

Procedure

To a mixture of lead tetraacetate (2.15 g, 4.85 mmol) and mercuric diacetate (0.15 g, 0.47 mmol), thoroughly flushed with nitrogen, is added anhydrous chloroform (6 ml). This mixture is warmed to 40° C., and 4′-chloro-4-ethylbiphenyl-3-ylboronic acid (1.17 g, 4.50 mmol) is added in one portion and the suspension is heated at this temperature for 5 hours. The mixture is then cooled to room temperature, concentrated to a small volume and triturated with hexanes and filtered to yield crude 4′-chloro-4-ethylbiphenyl-3-yllead triacetate (2.70 g).

Workup

  1. customthoroughly flushed with nitrogen
  2. additionis added anhydrous chloroform (6 ml)
  3. temperaturethe suspension is heated at this temperature for 5 hours
  4. temperatureThe mixture is then cooled to room temperature
  5. concentrationconcentrated to a small volume
  6. customtriturated with hexanes
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ed8747b4805942959f2a968b65542222
Source dataset
uspto-grants-2015_04
Patent number
US09006429B2

Reaction notes

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