Reaktion #84747

Reaktionsgleichung

2-amino-5-bromo-3-fluorobenzoic acid

borohydride

→

title compound

Ausbeute 95.0%

(2-amino-5-bromo-3-fluorophenyl)methanol

Ausbeute 95.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with methanol (150 mL)
2. 2
   Einengenconcentrated in vacuum
3. 3
   workup.ADDITIONdiluted with aqueous sodium bicarbonate (400 mL)
4. 4
   Extraktionextracted with ethyl acetate (200 mL*3)
5. 5
   SonstigeThe organic layers were separated
6. 6
   Waschenwashed with water (200 mL) and brine (200 mL)
7. 7
   Trocknendried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated

Vorschrift

To a solution of 2-amino-5-bromo-3-fluorobenzoic acid (14.5 g, 62.2 mmol) in THF (150 mL) at 0° C. was added borohydride in THF (1 M, 310 mL), and the reaction mixture was stirred at room temperature overnight. The reaction was quenched with methanol (150 mL), concentrated in vacuum, diluted with aqueous sodium bicarbonate (400 mL) and extracted with ethyl acetate (200 mL*3). The organic layers were separated, combined, washed with water (200 mL) and brine (200 mL), dried over sodium sulfate, filtered and concentrated to afford the title compound (13.0 g, crude), which was directly used in the next step without the further purification. MS (ES+) C7H7BrFNO requires: 219, 221, found: 220, 222 [M+H]+.

Quelle