تفاعل #2348109

معادلة التفاعل

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

المردود 81.0%

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

المردود 81.0%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter the addition
2. 2
   درجة الحرارةthe reaction was warmed to room temperature
3. 3
   أخرىThe reaction was quenched by the addition of 5-10 mL water
4. 4
   أخرىVolatile solvent was removed under vacuum
5. 5
   ترشيحthe crude product was filtered
6. 6
   غسيلwashed with water
7. 7
   درجة الحرارةThe solid was refluxed in a mixture of acetone and ethanol for 15 minutes
8. 8
   درجة الحرارةAfter cooling to room temperature
9. 9
   ترشيحthe purified product was filtered
10. 10
    غسيلwashed with acetone and ethanol
11. 11
    أخرىThe solid was dried under high vacuum

الإجراء التجريبي

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.

المصدر