반응 #710539

반응 방정식

N-chlorosuccinimide

thioacetic acid S-(4-bromo-benzyl) ester

HCl

Water

→

(4-bromo-phenyl)-methanesulfonyl chloride

용매

acetonitrile

acetonitrile

반응 조건

후처리

1. 1
   기타the reaction
2. 2
   workup.ADDITIONThe remaining solution was added
3. 3
   기타reaction
4. 4
   workup.WAITleft
5. 5
   온도to warm to room temperature for 10 minutes
6. 6
   온도The mixture was cooled to 0° C.
7. 7
   추출the product was extracted with EtOAc
8. 8
   세척washed with brine
9. 9
   건조dried with Na2SO4
10. 10
    농축concentrated

실험 절차

To a solution of N-chlorosuccinimide (3.95 g, 29.6 mmol) in acetonitrile (11.6 mL) and 1 M HCl (2.31 mL) at 0° C. was slowly added a solution of thioacetic acid S-(4-bromo-benzyl) ester (1.81 g, 7.39 mmol) in acetonitrile (6.3 mL) over 60 minutes whilst allowing the reaction to warm to 15° C. The remaining solution was added and reaction left to warm to room temperature for 10 minutes. The mixture was cooled to 0° C. and stirred for 1 hour. Water was added and the product was extracted with EtOAc, washed with brine, dried with Na2SO4, concentrated to give (4-bromo-phenyl)-methanesulfonyl chloride (2.6 g, 9.6 mmol). 1H NMR (300 MHz, CDCl3): δ 7.60 (d, 2 H), 7.36 (d, 2 H), 4.81 (s, 2 H).

출처