4-Cyclopropyl-benzeneboronic acid synthesis
- Product Name:4-Cyclopropyl-benzeneboronic acid
- CAS Number:302333-80-8
- Molecular formula:C9H11BO2
- Molecular Weight:161.99
1124-14-7
126 suppliers
$11.00/250mg
302333-80-8
81 suppliers
$78.00/1g
Yield: 60%
Reaction Conditions:
Stage #1:1-bromo-4-cyclopropylbenzene with n-butyllithium;Triisopropyl borate in tetrahydrofuran;hexane;toluene at -70 - -20;
Stage #2: with hydrogenchloride in tetrahydrofuran;hexane;toluene at 20;
Steps:
VIII Example VIII 4-Cyclopropyl-phenylboronic acid
2.5 M solution of nButyllithium in hexane (14.5 mL) is added dropwise to 1-bromo-4-cyclopropyl-benzene (5.92 g) dissolved in THF (14 mL) and toluene (50 mL) and chilled to -70° C. The resultant solution is stirred at -70° C. for 30 min before triisopropyl borate (8.5 mL) is added. The solution is warmed to -20° C. and then treated with 4 M aqueous hydrochloric acid (15.5 mL). The reaction mixture is further warmed to room temperature and then the organic phase is separated. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried (sodium sulfate). The solvent is evaporated and the residue is washed with a mixture of ether and cyclohexane to give the product as a colorless solid. [0099] Yield: 2.92 g (60% of theory) [0100] Mass spectrum (ESI-): m/z=207 (Cl) [M+HCOO]-
References:
Boehringer Ingelheim Vetmedica GmbH;ECKHARDT, Matthias;BUTZ, Tanja;HIMMELSBACH, Frank;MARTIN, Hans-Juergen US2014/31540, 2014, A1 Location in patent:Paragraph 0097; 0098; 0099; 0100
5419-55-6
377 suppliers
$12.00/5g
1124-14-7
126 suppliers
$11.00/250mg
302333-80-8
81 suppliers
$78.00/1g
5419-55-6
377 suppliers
$12.00/5g
302333-80-8
81 suppliers
$78.00/1g
1219741-94-2
59 suppliers
$98.00/100mg
302333-80-8
81 suppliers
$78.00/1g