反応 #2028942

反応方程式

Methanesulfonyl chloride

methanesulfonyl chloride

4-bromo-3-chloroaniline

H2O

→

desired product

N-(4-bromo-3-chlorophenyl)methanesulfonamide

溶媒

pyridine

反応条件

後処理

1. 1
   温度cooling
2. 2
   その他The ice bath was removed immediately
3. 3
   workup.ADDITIONafter addition of the reagent
4. 4
   workup.STIRRINGAfter stirring for 0.5 h
5. 5
   抽出extracted with EtOAc (50 mL×3)
6. 6
   洗浄Combined organic layers were washed with brine (50 mL×2)
7. 7
   乾燥dried over Na2SO4
8. 8
   その他The solvent was removed in vacuo
9. 9
   その他to give the crude material (very light brown solid, 5.32 g)
10. 10
    その他The crude product was purified by a silica gel column chromatography (SiO2=80 g, EtOAc/hexane=1:1, Rf=0.3)

実験手順

In a 100 mL round bottomed flask 4-bromo-3-chloroaniline (A, 2.06 g, 10.0 mmol) was dissolve in pyridine (30 mL) at room temperature. Methanesulfonyl chloride (1.72 g, 15.0 mmol, 1.5 equiv) was added under an ice-water bath cooling. The ice bath was removed immediately after addition of the reagent. After stirring for 1.5 h, another methanesulfonyl chloride (0.57 g, 5.0 mmol, 0.5 equiv) was added at room temperature for the reaction to go to completion. After stirring for 0.5 h, the mixture was treated with H2O (50 mL) and extracted with EtOAc (50 mL×3). Combined organic layers were washed with brine (50 mL×2) and dried over Na2SO4. The solvent was removed in vacuo to give the crude material (very light brown solid, 5.32 g). The crude product was purified by a silica gel column chromatography (SiO2=80 g, EtOAc/hexane=1:1, Rf=0.3) to give the desired product as colorless crystals. The obtained crystals were recrystallized from EtOAc/hexane=1:2 (24 mL) to give the desired material [N-(4-bromo-3-chlorophenyl)methanesulfonamide (B)].

出典