Reaktion #1706878

Reaktionsgleichung

N-Iodosuccinimide

2-chloro-2′-fluoro-5-methoxybiphenyl

→

title compound

Ausbeute 60.9%

2-Chloro-2′-fluoro-4-iodo-5-methoxybiphenyl

Ausbeute 60.9%

Lösungsmittel

sulfuric acid

acetic acid

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepartitioned between dichloromethane (30 mL) and water (5 mL)
2. 2
   SonstigeThe organic phase was separated
3. 3
   Waschenwashed with water (2×5 mL), brine (5 mL)
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto give a red oil
8. 8
   SonstigeColumn chromatography purification on silica
9. 9
   Wascheneluting with dichloromethane:heptanes (1:9)

Vorschrift

N-Iodosuccinimide (683 mg, 3.04 mmol) was added to a solution of 2-chloro-2′-fluoro-5-methoxybiphenyl (Preparation 96, 749 mg, 3.16 mmol) in concentrated sulfuric acid (0.09 mL), acetic acid (4.7 mL) and dichloromethane (4.7 mL). The resulting mixture was stirred at room temperature for 18 hours and then partitioned between dichloromethane (30 mL) and water (5 mL). The organic phase was separated and washed with water (2×5 mL), brine (5 mL), dried over MgSO4, filtered and evaporated to give a red oil. Column chromatography purification on silica, eluting with dichloromethane:heptanes (1:9) gave the title compound (671 mg, 58%) as a colourless oil.

Quelle