Reaktion #513099

Reaktionsgleichung

2,6-Dichloro-3-fluoroacetophenone

Lithium aluminum hydride

NaOH

MgSO4

NaOH

→

1-(2,6-Dichloro-3-fluoro-phenyl)-ethanol

Ausbeute 98.3%

Lösungsmittel

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefor 10 min
2. 2
   TemperaturThe reaction was cooled in ice bath
3. 3
   workup.STIRRINGThe mixture was stirred at ambient temperature for 30 min
4. 4
   Filtrationthe mixture filtered
5. 5
   Sonstigeto remove solids
6. 6
   WaschenThe solids were washed with THF (50 mL)
7. 7
   Einengenthe filtrate was concentrated

Vorschrift

2,6-Dichloro-3-fluoroacetophenone (15 g, 0.072 mol) was stirred in THF (150 mL, 0.5M) at 0° C. using an ice bath for 10 min. Lithium aluminum hydride (from Aldrich, 2.75 g, 0.072 mol) was slowly added. The reaction was stirred at ambient temperature for 3 h. The reaction was cooled in ice bath, and water (3 mL) was added drop wisely followed by adding 15% NaOH (3 mL) slowly. The mixture was stirred at ambient temperature for 30 min. 15% NaOH (9 mL), MgSO4 were added and the mixture filtered to remove solids. The solids were washed with THF (50 mL) and the filtrate was concentrated to give 1-(2,6-Dichloro-3-fluoro-phenyl)-ethanol (14.8 gm, 95% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 1.45 (d, 3H), 5.42 (m, 2H), 7.32 (m, 1H), 7.42 (m, 1H).

Quelle