ChemicalBook CAS DataBase List 2,2'-BITHIOPHENE-5-BORONIC ACID

2,2'-BITHIOPHENE-5-BORONIC ACID synthesis

5synthesis methods

Product Name:2,2'-BITHIOPHENE-5-BORONIC ACID
CAS Number:132898-95-4
Molecular formula:C8H7BO2S2
Molecular Weight:210.08

121-43-7
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492-97-7 Synthesis

492-97-7
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132898-95-4
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$65.00/100 mg

Yield: 97%

Reaction Conditions:

Stage #1:2,2'-Bithiophene with n-butyllithium in tetrahydrofuran;hexane at -78; for 0.25 h;
Stage #2:Trimethyl borate in tetrahydrofuran;hexane at -78 - 20; for 3 h;
Stage #3: with hydrogenchloride in tetrahydrofuran;hexane;water

Steps:

72 Synthesis of (2,2′-bithiophen)-5-yl-boronic acid (109)
In a flame-dried, 3-neck, 250 mL rbf, 2,2′-bithiophene (5.0 g, 30.1 mmol) was dissolved in anhydrous THF (100 mL) and cooled to -78° C. (dry ice/acetone). A solution of n-BuLi in hexanes (2.5 M, 12.6 mL, 31.6 mmol) was added slowly over a period of 5 minutes. The reaction mixture was allowed to stir at -78° C. for 15 minutes, and then trimethyl borate (10.1 mL, 90 mmol) was added dropwise over a period of 5 minutes. The reaction was allowed to stir at -78° C. for 2 hours, then warm to RT and stir for a further 1 hour. The yellow reaction mixture was quenched by pouring it into a 10% HCl solution (250 mL). The mixture was extracted with ether (2×100 mL) and the combined organic portions were washed with water (500 mL), dried over MgSO₄, filtered and solvent removed by rotary evaporation. The resulting yellow solid was washed with water, filtered and air dried to afford ( 109) (6.15 g, 97%). The material was used in the next step without further purification.

References:

SWITCH MATERIALS, INC.;Branda, Neil Robin;Finden, Jeremy Graham;Gauthier, Simon James;Hayek, Ali;Hope-Ross, Kyle Andrew;Senior, James Daniel;Spantulescu, Andreea;Sviridov, Serguei US2014/256936, 2014, A1 Location in patent:Paragraph 0446

492-97-7 Synthesis

492-97-7
322 suppliers
$5.00/1g

132898-95-4
78 suppliers
$65.00/100 mg

References

121-43-7
381 suppliers
$13.00/25mL

492-97-7 Synthesis

492-97-7
322 suppliers
$5.00/1g