Phenol → HCID 19907329, compound

HRID 2371438Notes

Reaction equation

HRID 2371438 reaction equation
[OH-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:10][C:11]1[CH:22]=[CH:21][C:14]2[C:15](=O)[O:16]C(=O)[NH:18][C:13]=2[CH:12]=1.O1CCCC1>C(OCC)(=O)C>[F:10][C:11]1[CH:12]=[C:13]([NH2:18])[C:14](=[CH:21][CH:22]=1)[C:15]([O:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:16]

Participants

6

Reactant 4

HCID 996PhenolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 100581387-Fluoroisatoic anhydride

Product 1

HCID 19907329HCID 19907329, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydroxide (2 pellets; approx 0.15 g) was added to a mixture of phenol (1.08 g) and 7-fluoro-1H-3,1-benzoxazine-2,4-dione (2 g) followed by tetrahydrofuran (4 ml). The mixture was heated on a steam bath until gas evolution ceased. It was then cooled, diluted with ethyl acetate (100 ml), the liquid collected and washed with aqueous sodium carbonate, dried, treated with charcoal and evaporated. The crude product was recrystallised from diisopropyl ether/light petroleum to give phenyl 4-fluoroanthranilate, m.p. 69°-70°. (Compound 3).

Workup

  1. temperatureThe mixture was heated on a steam bath until gas evolution
  2. temperatureIt was then cooled
  3. customthe liquid collected
  4. washwashed with aqueous sodium carbonate
  5. customdried
  6. additiontreated with charcoal
  7. customevaporated
  8. customThe crude product was recrystallised from diisopropyl ether/light petroleum

Sources & evidence

ORD record
ord-c6d2fe7a3f0c4934bf81bac1e8e46a19
Source dataset
uspto-grants-1992_03
Patent number
US05093364

Reaction notes

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