Reacción #1605814

Ecuación de reacción

2-Phenyl-4-bromoaniline

tert-butyl-3-butenoate

tri-(o-tolyl)phosphine

diisopropylethylamine

→

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

Rendimiento 78.8%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónthe reaction mixture was filtered through celite
2. 2
   Lavadowashed with ethyl acetate (120 mL)
3. 3
   LavadoThe organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL)
4. 4
   Secadodried over sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe residue was purified by a silica gel column

Procedimiento

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).

Fuente