Реакция #327281

Уравнение реакции

Na2CO3

Naphthalene-2-boronic acid

3-bromoaniline

→

3-Naphthalen-2-yl-phenylamine

Выход 63.0%

Растворители

DME

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was refluxed overnight under argon flow
2. 2
   ДругоеThe solvent was removed under vacuum
3. 3
   Экстракцияextracted with CH2Cl2
4. 4
   СушкаThe organic phase was dried over MgSO4
5. 5
   Концентрированиеconcentrated under vacuum
6. 6
   ДругоеThe crude product was purified by silica column chromatography (5-20% EtOAc/hexanes)
7. 7
   ДругоеThe purification
8. 8
   ДругоеThe solvent was removed under vacuum from fractions
9. 9
   workup.ADDITIONcontaining product
10. 10
    Другоеresulting in 0.063 g in 63% yield

Методика

Naphthalene-2-boronic acid (0.119 g, 0.693 mmol) and 3-bromoaniline (0.05 mL, 0.462 mmol) in DME (2 mL) were combined in a flame-dried, round-bottom flask. Na2CO3 (2M, 0.485 mL, 0.970 mmol) and Pd(PPh3)4 (0.017 g, 0.014 mmol) were added to the stirred solution. The reaction was refluxed overnight under argon flow, and subsequently cooled to room temperature. The solvent was removed under vacuum and the resulting residue was resuspended in H2O and extracted with CH2Cl2. The organic phase was dried over MgSO4 and concentrated under vacuum. The crude product was purified by silica column chromatography (5-20% EtOAc/hexanes). The purification was monitored by TLC. The solvent was removed under vacuum from fractions containing product, resulting in 0.063 g in 63% yield.

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