Reacción #7865

Ecuación de reacción

NaHCO3

4-bromo-2-nitrophenol

tin(II) chloride dihydrate

→

2-amino-4-bromophenol

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was heated
2. 2
   Temperaturaat reflux
3. 3
   workup.ADDITIONpoured over ice
4. 4
   ExtracciónThe aqueous layer was extracted with EtOAc (2×150 mL)
5. 5
   Lavadothe combined extracts washed with brine
6. 6
   Secadodried over MgSO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo

Procedimiento

To a stirred solution of 4-bromo-2-nitrophenol (5.00 g, 22.9 mmol) in MeOH (120 mL) was added tin(II) chloride dihydrate (15.53 g, 68.8 mmol). The reaction mixture was heated at reflux and monitored by LC/MS. When significant reduction was complete, the reaction mixture was cooled to rt, poured over ice, and made basic (pH 9) with 50% saturated NaHCO3. The aqueous layer was extracted with EtOAc (2×150 mL) and the combined extracts washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give 2-amino-4-bromophenol as a dark gray solid. 1H NMR (CDCl3, 300 MHz) δ 9.29 (br s, 1H), 6.71 (d, 1H), 6.56 (d, 1H), 6.49 (dd, 1H), 4.83 (br s, 2H).

Fuente