Reaction #46719

Reaction equation

4-amino-2-hydroxy benzoic acid methyl ester

4-bromobenzaldehyde

NaBH(OAc)3

NaHCO3

→

yellow solid

Yield 58.0%

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

Yield 58.0%

Solvents

HOAc

1,2-dichloroethane

Water

Conditions

Workup

1. 1
   OtherThe organic layer was isolated
2. 2
   Otherdried
3. 3
   Otherevaporated to dryness
4. 4
   Otherrecrystallised from isopropyl ether/dichloromethane/heptane

Procedure

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.

Source