Reaction #1563946

Reaction equation

H2SO4

1-(5-fluoro-2-hydroxy-3-nitrophenyl) ethanone

→

5-fluoro-3-nitrobenzene-1,2-diol

Solvents

1,4-Dioxane

Conditions

Workup

1. 1
   Temperaturemaintaining the temperature at 0° C.
2. 2
   workup.ADDITIONafter addition
3. 3
   Temperaturethe reaction mixture was warmed to 25° C.
4. 4
   workup.STIRRINGstirred for 16 h
5. 5
   OtherReaction mixture
6. 6
   Otherwas quenched with cold water, solid
7. 7
   Otherseparated
8. 8
   Filtrationwas collected by filtration
9. 9
   Filtrationfiltered
10. 10
    Otherto remove insoluble inorganic mass, ether layer
11. 11
    Washwas washed with cold water (2 to 3 times)
12. 12
    Dryingdried over anhydrous sodium sulphate
13. 13
    Concentrationconcentrated under reduced pressure
14. 14
    Otherto afford the crude sticky solid
15. 15
    OtherThe crude solid was triturated over n-Hexane
16. 16
    Filtrationfiltered

Procedure

H2SO4 (50 mL) was added to a solution of H3BO3 (89.3 g, 1.4 mol) in 1,4-Dioxane (300 mL) at 0° C. and stirred at 28° C. for 1 h. 1-(5-fluoro-2-hydroxy-3-nitrophenyl) ethanone (50 g, 289 mmol) was added portion wise to the above solution over 1 h, maintaining the temperature at 0° C., after addition was complete, the reaction mixture was warmed to 25° C. and stirred for 16 h. Reaction mixture was quenched with cold water, solid separated was collected by filtration. The solid was suspended in diethyl ether (500 mL) and filtered to remove insoluble inorganic mass, ether layer was washed with cold water (2 to 3 times) followed by brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude sticky solid. The crude solid was triturated over n-Hexane and filtered to afford 5-fluoro-3-nitrobenzene-1,2-diol (Int-50) as pale yellow solid. MS (ESI): m/z 171.9 (M−1).

Source