1,1'-Carbonyldiimidazole → 5-Fluoro-2(3H)-benzoxazolone

HRID 1945230Notes

Reaction equation

HRID 1945230 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11]>C(Cl)Cl.C(#N)C>[F:8][C:6]1[CH:5]=[CH:4][C:3]2[O:9][C:10](=[O:11])[NH:1][C:2]=2[CH:7]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 27359172-Amino-4-fluorophenol

Product 1

HCID 2872085-Fluoro-2(3H)-benzoxazolone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-amino-4-fluorophenol (4.0 g), carbonyldiimidazole (1.7 g) in DCM (100 ml) and acetonitrile (30 ml) was stirred at RT for 5 h. The solvent was removed under reduced pressure and the residue purified by chromatography on silica eluting with 30% ethylacetate/isohexane, yield 4.0 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by chromatography on silica eluting with 30% ethylacetate/isohexane, yield 4.0 g

Sources & evidence

ORD record
ord-595608a942784def9d11957363a8fb65
Source dataset
uspto-grants-2013_03
Patent number
US08394986B2

Reaction notes

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