Potassium Fluoride → HCID 66789964, compound

HRID 1672288Notes

Reaction equation

HRID 1672288 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[F-].[K+].Br[CH:15]([F:21])[C:16](OCC)=[O:17]>CN(C)C=O.C(OCC)(=O)C>[F:21][CH:15]1[C:16](=[O:17])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[O:11]1

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 2733407Acetic acid, 2-bromo-2-fluoro-, ethyl esterHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 66789964HCID 66789964, compoundYield 41.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 2-amino-5-nitrophenol (1.98 g) and potassium fluoride (2.24 g) in N,N-dimethylformamide (40 mL) was added ethyl bromofluoroacetate (2.85 g), and the mixture was stirred at 60° C. for 44 hours. After cooling, the reaction mixture was diluted with ethyl acetate, and the mixture was washed successively with water and brine. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (solvent; n-hexane/ethyl acetate=19/1→1/1) and triturated with n-hexane/diisopropylether to give 2-fluoro-7-nitro-2H-1,4-benzoxazin-3(4H)-one (1.14 g) as a yellow powder.

Workup

  1. temperatureAfter cooling
  2. washthe mixture was washed successively with water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by column chromatography on silica gel (solvent; n-hexane/ethyl acetate=19/1→1/1)
  6. customtriturated with n-hexane/diisopropylether

Sources & evidence

ORD record
ord-17d2fc05573c4f83b90a715af2485f78
Source dataset
uspto-grants-2011_08
Patent number
US07998956B2

Reaction notes

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