반응 #2348109

반응 방정식

Intermediate 3

2-(4-bromo-5-chloro-2-methoxyphenyl)-2,4-dihydro-5-(5-bromothien-2-yl)-3H-1,2,4-triazol-3-one

2-(4-Bromo-5-chloro-2-methoxyphenyl)-2,4-dihydro-5-(5-bromothien-2-yl)-3H-1,2,4-triazol-3-one

2-(4-bromo-5-chloro-2-methoxyphenyl)-2,4-dihydro-5-(5-bromothien-2-yl)-3H-1,2,4-triazol-3-one

BBr3

Intermediate 3

2-(4-bromo-5-chloro-2-methoxyphenyl)-2,4-dihydro-5-(5-bromothien-2-yl)-3H-1,2,4-triazol-3-one

dichloromethane

2-(4-bromo-5-chloro-2-methoxyphenyl)-2,4-dihydro-5-(5-bromothien-2-yl)-3H-1,2,4-triazol-3-one

→

desired product

수율 81.0%

2-(4-bromo-5-chloro-2-hydroxyphenyl)-2,4-dihydro-5-(5-bromothien-2-yl)-3H-1,2,4-triazol-3-one

수율 81.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition
2. 2
   온도the reaction was warmed to room temperature
3. 3
   기타The reaction was quenched by the addition of 5-10 mL water
4. 4
   기타Volatile solvent was removed under vacuum
5. 5
   여과the crude product was filtered
6. 6
   세척washed with water
7. 7
   온도The solid was refluxed in a mixture of acetone and ethanol for 15 minutes
8. 8
   온도After cooling to room temperature
9. 9
   여과the purified product was filtered
10. 10
    세척washed with acetone and ethanol
11. 11
    기타The solid was dried under high vacuum

실험 절차

2-(4-Bromo-5-chloro-2-methoxyphenyl)-2,4-dihydro-5-(5-bromothien-2-yl)-3H-1,2,4-triazol-3-one (Intermediate 3) (1.395 g) was suspended in anhydrous dichloromethane (20-25 mL/mmol of Intermediate 3) under argon and cooled to −78° C. A 1 M solution of BBr3 (9 mL) in anhydrous dichloromethane was added via a dropping funnel over a 45 minute period. After the addition was complete, the reaction was warmed to room temperature and stirred for 5 hours. The reaction was quenched by the addition of 5-10 mL water. Volatile solvent was removed under vacuum and the crude product was filtered and washed with water. The solid was refluxed in a mixture of acetone and ethanol for 15 minutes. After cooling to room temperature, the purified product was filtered and washed with acetone and ethanol. The solid was dried under high vacuum to yield 1.1 g (81%) of the desired product, Compound II.

출처