Reacción #64387

Ecuación de reacción

HCl

n-BuLi

4-ethylphenyl-t-butylsulfonamide

B(OiPr)3

→

titled compound

2-t-butylsulfonamido-5-ethylphenylboric acid

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONTo the mixture, containing the bright orange dianion at 0° C.
2. 2
   Temperaturato warm to rt
3. 3
   workup.STIRRINGstirred overnight
4. 4
   workup.STIRRINGthe mixture was stirred for 1 h
5. 5
   OtroThe solvent was removed under reduced pressure
6. 6
   Extracciónthe residue was extracted with EtOAc
7. 7
   LavadoThe organic was washed with 2N HCl, H2O and brine
8. 8
   SecadoThe organic was dried over anhydrous MgSO4
9. 9
   Concentraciónconcentrated in vacuo

Procedimiento

To a solution of 4-ethylphenyl-t-butylsulfonamide (6.44 g, 26.7 mmoL) in anhydrous THF (60 mL) cooled to -20° C. under N2 was added 2.5M n-BuLi solution (27 mL, 2.5 equiv). The mixture was warmed to rt and stirred for 2 h. To the mixture, containing the bright orange dianion at 0° C., was added B(OiPr)3 (9.3 mL, 1.5 equiv). The reaction was allowed to warm to rt and stirred overnight. The next day 2N HCl (3 mL) was added and the mixture was stirred for 1 h. The solvent was removed under reduced pressure and the residue was extracted with EtOAc. The organic was washed with 2N HCl, H2O and brine. The organic was dried over anhydrous MgSO4 and concentrated in vacuo to afford the titled compound. Rf=0.5 (1:1 EtOAc/Hex). The material was used in subsequent steps without further purification.

Fuente