Nitric Acid → 5-Fluoro-6-nitro-2,3-dihydro-1,3-benzoxazol-2-one

HRID 1058211

Reaction equation

HRID 1058211 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12](=[O:14])[NH:11][C:10]=2[CH:15]=1>O>[F:5][C:6]1[C:7]([N+:1]([O-:4])=[O:2])=[CH:8][C:9]2[O:13][C:12](=[O:14])[NH:11][C:10]=2[CH:15]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2872085-Fluoro-2(3H)-benzoxazolone

Product 1

HCID 112178355-Fluoro-6-nitro-2,3-dihydro-1,3-benzoxazol-2-oneYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

In a 500-ml flask, place 100 ml of concentrated nitric acid (70%) and warm to 45° C. Add 30.6 g (0.2 m) of 5-fluoro-benzoxazol-2-one (1a; X=F) and stir at 50° C. for 3 hrs. Add 240 ml of water slowly, and stir and cool to room temperature. Collect solid, wash with water, and dry in air to give 35.0 g (88%) of 5-fluoro-6-nitro-benzoxazol-2-one (2a; X=F) as pale yellow solids.

Workup

  1. customIn a 500-ml flask, place
  2. stirringstir
  3. temperaturecool to room temperature
  4. customCollect solid
  5. washwash with water
  6. customdry in air

Sources & evidence

ORD record
ord-9a5f5f647d1f4215a437c2010fcf77b0
Source dataset
uspto-grants-2003_02
Patent number
US06515176B1

Linked notes

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