Reaktion #46729

Reaktionsgleichung

1-methoxy-3-nonyl benzene

DMF

N-bromosuccinimide

→

1-Bromo-2-methoxy-nonyl benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe MeOH/ice bath was removed after 1 hour
2. 2
   workup.WAITthe reaction mixture was left overnight
3. 3
   workup.STIRRINGwith stirring
4. 4
   workup.ADDITIONThe reaction mixture was poured onto H2O (100 mL) and 10 M NaOH (aq)
5. 5
   workup.ADDITIONwas added
6. 6
   ExtraktionThe alkaline slurry was extracted with EtOAc (2×)
7. 7
   Waschenthe combined organic fractions washed with 1 M NaOH (aq.; 2×)
8. 8
   Trocknendried (MgSO4)
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated to dryness
11. 11
    SonstigeThe crude product was further purified by column chromatography (SiO2; EtOAc/PE80-100° C.=0:1→1:20)
12. 12
    Sonstigeto yield 9.8 g (quantitative) of product with satisfactory purity

Vorschrift

A solution of 1-methoxy-3-nonyl benzene (7.5 g; 32 mmol) in DMF (60 mL) was cooled to −10° C. and N-bromosuccinimide (5.42 g; 30 mmol) was added under stirring over 30 minutes. The MeOH/ice bath was removed after 1 hour and the reaction mixture was left overnight with stirring. The reaction mixture was poured onto H2O (100 mL) and 10 M NaOH (aq) was added. The alkaline slurry was extracted with EtOAc (2×) and the combined organic fractions washed with 1 M NaOH (aq.; 2×), dried (MgSO4), filtered and evaporated to dryness. The crude product was further purified by column chromatography (SiO2; EtOAc/PE80-100° C.=0:1→1:20) to yield 9.8 g (quantitative) of product with satisfactory purity.

Quelle