Реакция #587738

Уравнение реакции

2-Chloroaniline

5-bromo-2,3,4-trifluorobenzoic acid

i-Pr2NH

n-BuLi

→

desired product

Выход 82.0%

5-bromo-2-(2-chlorophenylamino)-3, 4-difluorobenzoic acid

Выход 82.0%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGAfter vigorous stirring for 10 minutes
2. 2
   ДругоеThe dry-ice bath was removed
3. 3
   workup.STIRRINGthe reaction mixture was stirred for 2 hours at room temperature
4. 4
   КонцентрированиеThe mixture was concentrated
5. 5
   workup.ADDITIONtreated with 10% aqueous HCl (120 mL)
6. 6
   Экстракцияextracted with EtOAc
7. 7
   Сушкаdried over MgSO4
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated
10. 10
    Другоеto give the crude solid which
11. 11
    Другоеwas triturated with boiling CH2Cl2 (125 mL)
12. 12
    ФильтрацияThe yellow solids were filtered
13. 13
    Другоеdried in vacuo

Методика

To a solution of i-Pr2NH (25.0 mL, 178 mmol) in THF (200 mL) at 0° C. was added n-BuLi (71.0 mL, 178 mmol, 2.5 M solution in hexanes). After stirring for 15 minutes, this solution was cooled to −78° C. 2-Chloroaniline (12.7 mL, 118 mmol) was added. After vigorous stirring for 10 minutes, a solution of 5-bromo-2,3,4-trifluorobenzoic acid (14.95 g, 58.63 mmol) in THF (30 mL) was added. The dry-ice bath was removed, and the reaction mixture was stirred for 2 hours at room temperature. The mixture was concentrated, treated with 10% aqueous HCl (120 mL), extracted with EtOAc, dried over MgSO4, filtered, and concentrated to give the crude solid which was triturated with boiling CH2Cl2 (125 mL). The yellow solids were filtered, and dried in vacuo to give the desired product (17.4 g, 82%).

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