Reaktion #46719

Reaktionsgleichung

4-amino-2-hydroxy benzoic acid methyl ester

4-bromobenzaldehyde

NaBH(OAc)3

NaHCO3

→

yellow solid

Ausbeute 58.0%

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

Ausbeute 58.0%

Lösungsmittel

HOAc

1,2-dichloroethane

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic layer was isolated
2. 2
   Sonstigedried
3. 3
   Sonstigeevaporated to dryness
4. 4
   Sonstigerecrystallised from isopropyl ether/dichloromethane/heptane

Vorschrift

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.

Quelle