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

HRID 72254Notes

Reaction equation

HRID 72254 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:35]=[CH:34][C:22]([C:23]2[CH:24]=[CH:25][C:26]([CH2:32][CH3:33])=[C:27](B(O)O)[CH:28]=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:35]=[CH:34][C:22]([C:23]2[CH:24]=[CH:25][C:26]([CH2:32][CH3:33])=[C:27]([Pb+3:17])[CH:28]=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-ethylbiphen-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 than cooled to room temperature, concentrated to a small volume and triturated with hexanes and filtered to yield crude 4′-chloro-4-ethylbiphen-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. temperaturethan cooled to room temperature
  5. concentrationconcentrated to a small volume
  6. customtriturated with hexanes
  7. filtrationfiltered

Sources & evidence

ORD record
ord-415ad0ab24f343119cbec2dad7fd40cb
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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