تفاعل #64387

معادلة التفاعل

HCl

n-BuLi

4-ethylphenyl-t-butylsulfonamide

B(OiPr)3

→

titled compound

2-t-butylsulfonamido-5-ethylphenylboric acid

المذيبات

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر