Реакция #645376

Уравнение реакции

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

2-fluoroaniline

LiHMDS

→

5-bromo-3,4-difluoro-2-(2-fluorophenylamino)benzoic acid

Выход 57.3%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred at this temperature for 4 h
2. 2
   КонцентрированиеThe mixture was concentrated
3. 3
   Другоеquenched with 10% HCl solution (70 ml)
4. 4
   Экстракцияextracted with EtOAc (2×200 ml)
5. 5
   СушкаThe combined organic solution was dried over MgSO4
6. 6
   Концентрированиеconcentrated to dryness
7. 7
   ДругоеPurification by trituration with boiling CH2Cl2

Методика

To a solution of 2-fluoroaniline (4.27 ml, 44.3 mmol) in THF (30 ml) at −78° C. was added LiHMDS (66.6 ml, 1 M in THF, 66.6 mmol) dropwise. The reaction mixture was stirred for 10 min and a solution of 5-bromo-2,3,4-trifluorobenzoic acid (5.63 g, 22.2 mmol) in THF (40 ml) was added to the mixture. The reaction was slowly warmed to room temperature and stirred at this temperature for 4 h. The mixture was concentrated, quenched with 10% HCl solution (70 ml), and extracted with EtOAc (2×200 ml). The combined organic solution was dried over MgSO4 and concentrated to dryness. Purification by trituration with boiling CH2Cl2 gave 4.40 g (57%) of 5-bromo-3,4-difluoro-2-(2-fluorophenylamino)benzoic acid as a yellow solid.

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