ChemicalBook CAS DataBase List 3-Carboxyphenylboronic acid

3-Carboxyphenylboronic acid synthesis

9synthesis methods

Product Name:3-Carboxyphenylboronic acid
CAS Number:25487-66-5
Molecular formula:C7H7BO4
Molecular Weight:165.94

150255-96-2
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25487-66-5
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$6.00/5g

Yield:25487-66-5 89%

Reaction Conditions:

Stage #1:(3‐cyanophenyl)boronic acid with potassium hydroxide in ethylene glycol at 175; for 3 h;
Stage #2: with hydrogenchloride in water;ethylene glycol; pH=2 - 3

Steps:

1 1. Preparation of 3-carboxyphenylboronic acid
1. Preparation of 3-carboxyphenylboronic acid 10 g (68 mmol) of 3-cyanophenylboronic acid and 15.26 g (272 mmol, 4 eq.) of potassium hydroxide powder were suspended in 40 ml of ethylene glycol and heated to 175° C. After three hours, the reaction mixture was allowed to cool and was diluted with 60 ml of water. The pH was adjusted to 2-3 with 32% hydrochloric acid, which precipitated the 3-carboxyphenylboronic acid in colorless crystalline form, which was isolated by filtering it off with suction. The crystals were washed with water and dried under a gentle vacuum at 35° C. The yield was 10.04 g (60.5 mmol, 89%).

References:

Meudt, Andreas;Nerdinger, Sven;Lehnemann, Bernd Wilhelm US2009/286995, 2009, A1 Location in patent:Page/Page column 4

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