반응 #69679

반응 방정식

2-(p-toluensulphonyl)-5-chloroisoindoline

phenol

hydrobromic acid

propionic acid

→

5-chloro-2,3-dihydro-1H-isoindole hydrochloride

수율 97.2%

용매

water

반응 조건

후처리

1. 1
   온도mixture was heated
2. 2
   온도at reflux for 6 hours
3. 3
   기타The resultant reaction mixture
4. 4
   추출extracted twice with 50 ml of ethyl acetate
5. 5
   추출extracted with ethyl acetate three times
6. 6
   농축The extract was concentrated
7. 7
   workup.ADDITIONthe crude product was diluted with 4N HCl/dioxane
8. 8
   기타before evaporating the HCl
9. 9
   기타re-evaporating with toluene three times

실험 절차

1.0 g of 2-(p-toluensulphonyl)-5-chloroisoindoline and 1.0 g of phenol were added to a mixture of 8 ml of 48% hydrobromic acid and 1.4 ml of propionic acid, and then mixture was heated at reflux for 6 hours. The resultant reaction mixture was diluted with 10 ml of water and extracted twice with 50 ml of ethyl acetate. The water layer was basified with aqueous sodium hydroxide solution and extracted with ethyl acetate three times. The extract was concentrated and the crude product was diluted with 4N HCl/dioxane and stirred for 15 minutes before evaporating the HCl and then re-evaporating with toluene three times to give 0.3 g of 5-chloro-2,3-dihydro-1H-isoindole hydrochloride as a black solid. MS: [M+H]+ 153-15

출처