Reaction #586184

Reaction equation

5-bromo-2-(3,4-dichloro-phenoxy)-benzaldehyde

MeNH2

NaBH4

→

desired product

Yield 97.0%

[5-Bromo-2-(3,4-dichloro-phenoxy)-benzyl]-methyl-amine

Yield 97.0%

Solvents

MeOH

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled to 0° C.
2. 2
   Concentrationthe mixture was concentrated
3. 3
   workup.ADDITIONthe residue was diluted with 1 N NaOH
4. 4
   Extractionextracted with DCM
5. 5
   DryingThe combined organic layers were dried (Na2SO4)
6. 6
   Concentrationconcentrated
7. 7
   OtherThe crude product was purified by FCC

Procedure

To a mixture of 5-bromo-2-(3,4-dichloro-phenoxy)-benzaldehyde (4.74 g, 13.8 mmol) in MeOH (250 mL) was added MeNH2 (40% aq.; 20 mL, 260 mmol), and the resulting mixture was stirred at rt until homogeneous. The mixture was cooled to 0° C. and treated with NaBH4 (1.05 g, 27.8 mmol) portionwise. After 24 h, the mixture was concentrated and the residue was diluted with 1 N NaOH and extracted with DCM. The combined organic layers were dried (Na2SO4) and concentrated. The crude product was purified by FCC to provide the desired product (4.80 g, 97%). MS (ESI): mass calcd. for C14H12BrCl2NO, 358.95; m/z found, 360.1 [M+H]+. 1H NMR (CDCl3): 7.61 (d, J=2.5, 1H), 7.40-7.37 (m, 2H), 7.03 (d, J=2.8, 1H), 6.82-6.79 (m, 2H), 3.72 (s, 2H), 2.44 (s, 3H), 1.30-1.21 (m, 1H).

Source