Pyridine → 4-Cyanophenylboronic acid

HRID 1369185Notes

Reaction equation

HRID 1369185 reaction equation
S(O)(O)(=O)=O.NO.[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([B:16]([OH:18])[OH:17])=[CH:12][CH:11]=1)=O.[N:19]1C=CC=CC=1>O.C1(C)C=CC=CC=1>[C:8]([C:10]1[CH:15]=[CH:14][C:13]([B:16]([OH:18])[OH:17])=[CH:12][CH:11]=1)#[N:19]

Participants

6

Reactant 3

HCID 1049PyridineHCID 159255Hydroxylamine, sulfate (1:1)HCID 5910734-Formylphenylboronic Acid

Product 1

HCID 27343264-Cyanophenylboronic acidYield 144.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

17 g (100 mmol) of hydroxylamine sulfate were added at 70° C. to 15 g (100 mmol) of 4-formylphenylboronic acid, 10 g of water, 5 g (60 mmol) of pyridine and 200 ml of toluene. The mixture was then refluxed on a water separator. When all the water had been removed, the pyridinium salts were separated off, giving 12.7 g (87%) of 4-cyanophenylboronic acid.

Workup

  1. customWhen all the water had been removed
  2. customthe pyridinium salts were separated off

Sources & evidence

ORD record
ord-e35822cf005646279ebdb67b4f90ad0a
Source dataset
uspto-grants-2003_06
Patent number
US06576789B1

Reaction notes

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