Реакция #2348109

Уравнение реакции

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

Выход 81.0%

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

Выход 81.0%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Температураthe reaction was warmed to room temperature
3. 3
   ДругоеThe reaction was quenched by the addition of 5-10 mL water
4. 4
   ДругоеVolatile solvent was removed under vacuum
5. 5
   Фильтрацияthe crude product was filtered
6. 6
   Промывкаwashed with water
7. 7
   ТемператураThe solid was refluxed in a mixture of acetone and ethanol for 15 minutes
8. 8
   ТемператураAfter cooling to room temperature
9. 9
   Фильтрацияthe purified product was filtered
10. 10
    Промывкаwashed with acetone and ethanol
11. 11
    ДругоеThe solid was dried under high vacuum

Методика

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.

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