ChemicalBook CAS DataBase List 4-Fluoro-2-methylphenylboronic acid

4-Fluoro-2-methylphenylboronic acid synthesis

4synthesis methods

Product Name:4-Fluoro-2-methylphenylboronic acid
CAS Number:139911-29-8
Molecular formula:C7H8BFO2
Molecular Weight:153.95

5419-55-6
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452-63-1 Synthesis

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139911-29-8
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$6.00/1g

Yield: 61.5%

Reaction Conditions:

Stage #1:2-Bromo-5-fluorotoluene with n-butyllithium in tetrahydrofuran;hexane at -78; for 1 h;
Stage #2:Triisopropyl borate in tetrahydrofuran;hexane for 1 h;

Steps:

1 Example 1: synthesis of 2-methyl-4-fluorophenylboronic acid
In a solution of 2-bromo-5-fluorotoluene (250 g) in tetrahydrofuran (250 ml) and n- hexane (250 ml) was added n-butyl lithium (991.5 ml) drop wise at -78°C in a dry-ice bath. The solution was stirred for an hour. Triisopropyl borate (373.11 g) was added drop wise and reaction was stirred for further an hour. The resulting solution was diluted with aqueous sodium hydroxide and then washed with n-heptane. The pH of the aqueous layer was adjusted to pH 2-3 using hydrochloric acid and then extracted with ethyl acetate. The organic layer was concentrated under vacuum. This was dissolved in ethyl acetate at about 40°C and to this heptane was added to obtain 2- methyl-4-fluorophenylboronic acid. Yield: 61.5%; HPLC purity: 99.00%.

References:

GLENMARK PHARMACEUTICALS LIMITED;KUDUVA, Srinivasan Subramanian;-, Rajender;CHORAGHE, Mahendra Joma;NAIK, Samir;BHIRUD, Shekhar Bhaskar WO2017/125835, 2017, A1 Location in patent:Paragraph 00117

5419-55-6
378 suppliers
$12.00/5g

452-63-1 Synthesis

452-63-1
343 suppliers
$11.00/25g