Reaktion #219433

Reaktionsgleichung

Methyl 2-fluoro-6-nitrobenzoate

→

methyl 2-amino-6-fluorobenzoate

Lösungsmittel

EtOH HOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture was refluxed under N2 for 2 hrs
2. 2
   Sonstigethe brown suspension was partitioned between H2O (30 mL) and Et2O (100 mL)
3. 3
   SonstigeAfter separation
4. 4
   Extraktionthe aqueous solution was extracted with Et2O (50 mL)
5. 5
   WaschenThe combined organic layers were washed with 1N NaOH (3×50 mL), brine (50 mL)
6. 6
   Sonstigedried on MgSO4
7. 7
   Einengenconcentrated on rotary vacuum

Vorschrift

Methyl 2-fluoro-6-nitrobenzoate (715 mg, 3.59 mmol) was dissolved in EtOH/HOAc/(10 mL/10 mL), followed by addition of iron powder (602 mg, 10.8 mmol) at room temperature. The resulting mixture was refluxed under N2 for 2 hrs. After cooling down to room temperature, the brown suspension was partitioned between H2O (30 mL) and Et2O (100 mL). After separation, the aqueous solution was extracted with Et2O (50 mL). The combined organic layers were washed with 1N NaOH (3×50 mL), brine (50 mL), dried on MgSO4, and concentrated on rotary vacuum to afford the expected product, methyl 2-amino-6-fluorobenzoate, an colorless oil which became wax-type solid on standing. The crude compound was pure enough to be used in next step without further purification; 1H NMR (400 MHz, CDCl3) δ ppm 3.89 (s, 3 H), 5.67 (s, 2 H), 6.34 (ddd, J=11.58, 8.06, 1.01 Hz, 1 H), 6.41 (d, J=8.31 Hz, 1 H), 7.13 (td, J=8.18, 5.79 Hz, 1 H); Mass spec. 170.06 (MH+), Calc. for C8H8FNO2 169.05.

Quelle