Ammonia → 4-Carboxyphenylboronic Acid

HRID 1369186Notes

Reaction equation

HRID 1369186 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=1)#N.[OH-:12].[K+].N.[OH2:15]>CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=1)([OH:15])=[O:12]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 14797Potassium HydroxideHCID 27343264-Cyanophenylboronic acid

Product 1

HCID 3121834-Carboxyphenylboronic AcidYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

14.5 g (100 mmol) of 4-cyanophenylboronic acid were dissolved in a mixture of 11 g (200 mmol) of potassium hydroxide and 10 g of water in 100 ml of methanol, and the mixture was refluxed until the evolution of ammonia gas was complete, giving 14.9 g (90 mmol) of 4-carboxyphenylboronic acid.

Sources & evidence

ORD record
ord-b8cb560356334af59a8a0ad6a337fc83
Source dataset
uspto-grants-2003_06
Patent number
US06576789B1

Reaction notes

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