Reaction #586383

Reaction equation

sodium bisulfite

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

sodium bromate

EtOAc

sodium bisulfite

→

title compound

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

Solvents

water

Conditions

Workup

1. 1
   Otherorganic layer separated
2. 2
   Washwashed with aqueous saturated solution of sodium bicarbonate
3. 3
   DryingThe organic phase is dried with magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated at reduced pressure
6. 6
   Otherto afford

Procedure

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]).

Source