4''-PROPYL-3-FLUOROBIPHENYL-4-BORONIC ACID synthesis
- Product Name:4''-PROPYL-3-FLUOROBIPHENYL-4-BORONIC ACID
- CAS Number:909709-42-8
- Molecular formula:C15H16BFO2
- Molecular Weight:258.1
5419-55-6
948044-01-7
909709-42-8
The general procedure for the synthesis of (3-fluoro-4'-propyl-[1,1'-biphenyl]-4-yl)boronic acid from triisopropyl borate and 3-fluoro-4-propylbiphenyl was as follows: 3-fluoro-4-propylbiphenyl (22.2 g, 0.104 mol) and 150 mL of tetrahydrofuran were added to a reaction vessel equipped with a dropping funnel. The mixture was heated to 70 °C, followed by the slow dropwise addition of 124 mL of sec-butyllithium solution (1.0 mol/L). The reaction mixture was stirred at 70 °C for 2 h. Triisopropyl borate (25.3 g, 0.135 mol) was added dropwise. After continued stirring for 2 hours, the reaction mixture was cooled to 0 °C and 300 mL of 10% hydrochloric acid solution was added slowly and dropwise. After stirring for 1 h at room temperature, aqueous washing was performed to remove the salts. Eventually, by concentration and drying treatment, (3-fluoro-4'-propyl-[1,1'-biphenyl]-4-yl)boronic acid (25.7 g, 0.0995 mol) was obtained.
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Yield:909709-42-8 65%
Reaction Conditions:
Stage #1: 3-fluoro-1-(4-propylphenyl)benzenewith n-butyllithium in tetrahydrofuran at -80;Inert atmosphere;
Stage #2: Trimethyl borate in tetrahydrofuran;Inert atmosphere;
Stage #3: waterwith hydrogenchloride in tetrahydrofuran at 0;Inert atmosphere;
Steps:
1.e; 6.e; 7.e
e) Dissolve 214g (1mol) of the product obtained in step d) in 2L of tetrahydrofuran, and replace the air with nitrogen.Cool down to -80, add 443ml (1.1mol) n-butyllithium dropwise,Obtain the lithium reagent. After the addition, add 125g (1.2mol) trimethyl borate in 500ml tetrahydrofuran solution to replace lithium. After the natural temperature rises to 0°C,Pour into 2L of water, add 200ml of concentrated hydrochloric acid, separate, extract, wash with water, and evaporate to dryness to obtain 168g product with a yield of 65%.
References:
CN107312549,2021,B Location in patent:Paragraph 0088-0092; 0098; 0148; 0151-0153; 0158; 0160; ...
121-43-7
380 suppliers
$14.00/25mL
948044-01-7
19 suppliers
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909709-42-8
132 suppliers
$18.60/250mg
5419-55-6
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$12.00/5g
948044-01-7
19 suppliers
inquiry
909709-42-8
132 suppliers
$18.60/250mg
5419-55-6
388 suppliers
$12.00/5g
948044-01-7
19 suppliers
inquiry
7732-18-5
499 suppliers
$13.50/100ML
909709-42-8
132 suppliers
$18.60/250mg
688-71-1
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948044-01-7
19 suppliers
inquiry
909709-42-8
132 suppliers
$18.60/250mg