반응 #67500

반응 방정식

sulfur dioxide

Hydrochloric acid

sodium nitrite

2-Amino-6-difluoromethoxy-benzonitrile

→

2-Cyano-3-difluoromethoxy-benzenesulfonyl chloride

수율 91.0%

용매

acetic acid

water

Water

acetic acid

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting mixture is stirred at ambient temperature for 2 hours
2. 2
   추출extracted three times with dichloromethane
3. 3
   건조The combined organic phases are dried over sodium sulfate
4. 4
   농축concentrated

실험 절차

2-Amino-6-difluoromethoxy-benzonitrile (6.4 g, 35 mmol) is dissolved in glacial acetic acid (50 ml). Hydrochloric acid (37%, 12.7 g) is added dropwise at ambient temperature. This mixture is cooled to 5° C. and a solution of sodium nitrite (2.5 g, 36.4 mmol) in Water (8 ml) is added dropwise. The reaction mixture is stirred at 0° C. for 1 hour. The resulting diazonium salt solution is added dropwise at ambient temperature to a mixture of glacial acetic acid (100 ml) saturated at ambient temperature with sulfur dioxide and a solution of CuCl2 (2.18 g, 16.2 mmol) in water (5 ml). The resulting mixture is stirred at ambient temperature for 2 hours. The reaction mixture is poured into an ice/water and extracted three times with dichloromethane. The combined organic phases are dried over sodium sulfate and concentrated to give 2-Cyano-3-difluoromethoxy-benzenesulfonyl chloride (8.5 g, 91% yield) which is used without further purification. 1H-NMR (CDCl3, 400 MHz): 8.10 (d, 1H), 7.85 (t, 1H), 7.75 (d, 1H), 6.75 (t, 1H) ppm.

출처