Reacción #46719

Ecuación de reacción

4-amino-2-hydroxy benzoic acid methyl ester

4-bromobenzaldehyde

NaBH(OAc)3

NaHCO3

→

yellow solid

Rendimiento 58.0%

4-(4-Bromo-benzylamino)-2-hydroxy-benzoic acid methyl ester

Rendimiento 58.0%

Disolventes

HOAc

1,2-dichloroethane

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe organic layer was isolated
2. 2
   Otrodried
3. 3
   Otroevaporated to dryness
4. 4
   Otrorecrystallised from isopropyl ether/dichloromethane/heptane

Procedimiento

To a solution of 4-amino-2-hydroxy benzoic acid methyl ester (836 mg; 5 mmol) and 4-bromobenzaldehyde (926 mg; 5 mmol) in 1 M HOAc in 1,2-dichloroethane (5 mL) was added at once NaBH(OAc)3 (1.49 g; 7 mmol) and the reaction mixture was stirred at room temperature overnight. Water (25 mL) was added and the inhomogeneous mixture was neutralized using solid NaHCO3. The organic layer was isolated, dried, evaporated to dryness and recrystallised from isopropyl ether/dichloromethane/heptane to yield 970 mg (58%) of a yellow solid. NMR and GC-MS in accordance with structure.

Fuente