ChemicalBook CAS DataBase List phenyl-D5-boronic acid

phenyl-D5-boronic acid synthesis

7synthesis methods

Product Name:phenyl-D5-boronic acid
CAS Number:215527-70-1
Molecular formula:C6H7BO2
Molecular Weight:121.93

Phenyl-D5-boronic acid is a boronic acid compound that can be used in the Suzuki reaction. Phenyl-D5-boronic acid can be synthesised by the reaction of d5-bromobenzene as a starting material, brominated and then reacted with biboronic acid pinacol ester.

4165-57-5 Synthesis

4165-57-5
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$56.29/2g

215527-70-1
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$85.00/250mg

Yield:215527-70-1 98%

Reaction Conditions:

Stage #1:bromobenzene-d5 with n-butyllithium;triethyl borate in tetrahydrofuran at -78 - 20; for 4 h;
Stage #2: with hydrogenchloride;water in tetrahydrofuran at 0 - 20; for 1 h;

Steps:

1.3
(3) Preparation of N,N-di-naphtalen-l-yl-teφhenyl-4,4'-diamine-dl2 [63]1 n-BuLιPd₂(dba)₃ (0 03 eq)[64] 10 g (61.7 mmol) of bromobenzene-d5 was dissolved in 300 mL of tetrahydrofuran, and then the temperature of the reaction solution was maintained at -78°C. 57.8 mL (92.6 mmol) of 1.6M n-BuLi was then slowly added thereto, and the resulting solution EPO was refluxed while stirring for at -78°C 1 hour, to which 21 mL (123.4 mmol) of tri- ethylborate was slowly added. The reaction mixture was allowed to reach to room temperature, and then stirred for 3 hours. After IN HCl was added to the reaction mixture at 0°C, the reaction mixture was stirred for additional one hour at room temperature. After the reaction mixture was extracted with ethyl acetate, organic layers were dried with MgSO 4 and then filtered. The filtrate was concentrated, thereby obtaining 7.7 g (yield: 98%) of the desired compound, phenylboronic acid-d5, as a pale yellow solid.

References:

DOOSAN CORPORATION WO2006/121237, 2006, A1 Location in patent:Page/Page column 7-8

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