ChemicalBook CAS DataBase List 4-Trifluoromethylphenylboronic acid

4-Trifluoromethylphenylboronic acid synthesis

12synthesis methods

Product Name:4-Trifluoromethylphenylboronic acid
CAS Number:128796-39-4
Molecular formula:C7H6BF3O2
Molecular Weight:189.93

67-56-1 Synthesis

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67-56-1
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131765-96-3
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$42.79/1g

402-43-7 Synthesis

402-43-7
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128796-39-4
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$10.00/5g

Yield:128796-39-4 90% Reaction Conditions:

Stage #1:dicyclohexylamine borane complex;p-trifluoromethylphenyl bromide with magnesium in tetrahydrofuran at 70;
Stage #2:methanol in tetrahydrofuran at 0; for 1 h;
Stage #3: with hydrogenchloride;water in methanol at 20; for 1 h;

Steps:

Addition under Barbier conditions (procedure A)
General procedure: A solution in THF (4 mL) of DIPAB (863 mg, 7.5 mmol), Mg (182 mg, 7.5 mmol) and arylbromide (5 mmol) was stirred at 70 °C until no starting arylbromide remains (TLC). The reaction mixture was cooled down to 0 °C and quenched slowly with 7 mL of MeOH. After 1h, volatile were removed under reduced pressure and the resulting solid was dissolved in 1N HCl/MeOH (7/3). After 1h at room temperature, 100 mL of AcOEt were added, the organic phase was washed with 1N HCl (30 mL) and brine (3×30 mL). Organic phases were concentrated under reduced pressure yielding a solid which was recrystallized from H₂O.

References: Marciasini, Ludovic D.;Richard, Jimmy;Cacciuttolo, Bastien;Sartori, Guillaume;Birepinte, Melodie;Chabaud, Laurent;Pinet, Sandra;Pucheault, Mathieu [Tetrahedron,2019,vol. 75,# 2,p. 164 - 171]