Nitric Acid → 6-fluoro-5-nitro-2(3H)-benzoxazolone

HRID 414635Notes

Reaction equation

HRID 414635 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[F:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 144573586-Fluoro-1,3-benzoxazol-2(3H)-one

Product 1

HCID 137721116-fluoro-5-nitro-2(3H)-benzoxazoloneYield 85%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution cf 6-fluoro-2(3H)-benzoxazolone (1.0 g) in 80% aqueous sulfuric acid (6.5 g) was cooled to 0° to 5° C., and 60% nitric acid (0.8 g) was gradually added thereto at 0° to 5° C. The resultant mixture was stirred at the same temperature for 30 minutes and poured onto ice water. The precipitated crystals were collected by filtration, washed with water and dried to give 6-fluoro-5-nitro-2(3H)-benzoxazolone (1.1 g). m.p., 175.4° C. 1H-NMR (CDCl3 +DMSO-D6) δ ppm: 4.0 (1H, broad), 6.8-7.9 (3H, m).

Workup

  1. customat 0° to 5° C
  2. additionpoured onto ice water
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-399878f95d164f8ea6458e46497d883e
Source dataset
uspto-grants-1988_12
Patent number
US04792605

Reaction notes

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