Réaction #1605814

Équation de réaction

2-Phenyl-4-bromoaniline

tert-butyl-3-butenoate

tri-(o-tolyl)phosphine

diisopropylethylamine

→

tert-butyl (3E)-4-(3-amino-4-phenylphenyl)-3-butenoate

Rendement 78.8%

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   Filtrationthe reaction mixture was filtered through celite
2. 2
   Lavagewashed with ethyl acetate (120 mL)
3. 3
   LavageThe organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL)
4. 4
   Séchagedried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutreThe residue was purified by a silica gel column

Mode opératoire

2-Phenyl-4-bromoaniline (564.7 mg, 2.28 mmol) was dissolved in N,N-dimethylformamide (25 mL) and, at room temperature, thereto were added tert-butyl-3-butenoate (582.5 mg, 4.10 mmol), tri-(o-tolyl)phosphine (1.87 g, 6.16 mmol), and diisopropylethylamine (0.78 mL, 4.56 mmol). The reaction mixture was deaerated, palladium acetate (67.4 mg, 0.30 mmol) was added, and the mixture was deaerated again. After stirring at 90° C. overnight, the reaction mixture was filtered through celite and washed with ethyl acetate (120 mL). The organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL), thereafter dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by a silica gel column to obtain tert-butyl (3E)-4-(3-amino-4-phenylphenyl)-3-butenoate (555.8 mg).

Source