Reaktion #1154020

Reaktionsgleichung

2-fluoro-5-bromobenzyl alcohol

triphenylphosphine

carbon tetrabromide

→

desired title intermediate

Ausbeute 76.0%

2-fluoro-5-bromobenzyl bromide

Ausbeute 76.0%

Lösungsmittel

diethy ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was then stirred at ambient temperature for about 19 additional hours
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Waschenwashed with cold diethyl ether
4. 4
   SonstigeThe filtrate was evaporated
5. 5
   Sonstigeyielding a light yellow oil
6. 6
   SonstigeThe oil was further purified by chromatography on a silica gel with hexanes
7. 7
   SonstigeThe desired fractions were purified by evaporation

Vorschrift

In a 250 ml round bottom flask, under a nitrogen atmosphere, 2-fluoro-5-bromobenzyl alcohol (5.85 g, 28.5 mmol) was dissolved in diethy ether (125 ml). To this solution triphenylphosphine (9.73 g, 37.1 mmol) and carbon tetrabromide (12.30 g, 37.1 mmol) were added. The resulting mixture was stirred at ambient temperature for about three hours. The progress of the reaction was monitored by thin layer chromatography. The mixture was then stirred at ambient temperature for about 19 additional hours. The reaction mixture was filtered and washed with cold diethyl ether. The filtrate was evaporated, yielding a light yellow oil. The oil was further purified by chromatography on a silica gel with hexanes. The desired fractions were purified by evaporation to yield 5.8 grams of the desired title intermediate. The material slowly crystallized upon standing.

Quelle