ChemicalBook CAS DataBase List 2-BIPHENYLBORONIC ACID

2-BIPHENYLBORONIC ACID synthesis

13synthesis methods

Product Name:2-BIPHENYLBORONIC ACID
CAS Number:4688-76-0
Molecular formula:C12H11BO2
Molecular Weight:198.03

67-56-1 Synthesis

67-56-1
759 suppliers
$9.00/25ml

55124-35-1 Synthesis

55124-35-1
23 suppliers
$60.00/100mg

2052-07-5 Synthesis

2052-07-5
391 suppliers
$16.30/1g

4688-76-0
338 suppliers
$6.00/250mg

Yield:4688-76-0 94%

Reaction Conditions:

Stage #1: diisopropylamine boranewith magnesium;phenylmagnesium bromide in tetrahydrofuran at 20; for 0.166667 h;
Stage #2: 2-Bromobiphenyl in tetrahydrofuran at 70;
Stage #3: methanolFurther stages;

Steps:

PhMgBr dehydrogenation followed by the addition under Barbier conditions (procedure B)

General procedure: To a solution in THF (4 mL) of DIPAB (863 mg, 7.5 mmol) and Mg (182 mg, 7.5 mmol) were added a PhMgBr 1M THF solution (375 μL, 375μmol) at room temperature. After 10 min, 30 mL of anhydrous THF were added followed by the arylbromide (5 mmol). 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]