Reaktion #586383

Reaktionsgleichung

sodium bisulfite

2-Fluoro-1-methyl-4-nitro-benzene

sodium bromate

EtOAc

sodium bisulfite

→

title compound

1-Bromomethyl-2-fluoro-4-nitro-benzene

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeorganic layer separated
2. 2
   Waschenwashed with aqueous saturated solution of sodium bicarbonate
3. 3
   TrocknenThe organic phase is dried with magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated at reduced pressure
6. 6
   Sonstigeto afford

Vorschrift

To a solution of 2-Fluoro-1-methyl-4-nitro-benzene (1 g, 6.45 mmol) and sodium bromate (2.92 g, 19.33 mmol) in an EtOAc:water (12 mL:9 mL) mixture, is added dropwise via addition funnel a 3.85M solution of sodium bisulfite 5.20 mL, 19.33 mmol). The mixture is vigorously stirred for six days and then sodium bisulfite (10 mL) is added and organic layer separated and washed with aqueous saturated solution of sodium bicarbonate. The organic phase is dried with magnesium sulfate, filtered and evaporated at reduced pressure to afford a mixture of title compound and starting 2-fluoro-1-methyl-4-nitro-benzene in a 5:1 ratio (1H-NMR) which is used in the next step without further purification. ES+(m/z) 235 [M+H]).

Quelle